N-sulphonylaminoacetonitriles having pesticidal properties

ABSTRACT

The invention relates to compounds of the general formula (I) and, if appropriate, enantiomers thereof. The active compounds have advantageous pesticidal properties. They are suitable, in particular, for the control of parasites in warm-blooded animals.

The present invention relates to novel sulphonylaminoacetonitrilecompounds of the formula

in which

-   R₁ is aryl or heteroaryl, in each case unsubstituted or mono- or    polysubstituted by R₇, where the substituents can in each case be    identical or different if their number is greater than 1;-   R₂ is C₁-C₆alkyl, halo-C₁-C₆alkyl, C₃-C₈cycloalkyl,    halo-C₃-C₈cycloalkyl, NHR₈; aryl or heteroaryl, in each case    unsubstituted or mono- or polysubstituted by R₇, where the    substituents can in each case be identical or different if their    number is greater than 1, or pyrrolidinyl, piperidinyl,    imidazolidinyl, piperazinyl, pyrazolidinyl, morpholinyl, indolinyl    or isoindolinyl, in each case bonded via N;-   R₃ is hydrogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkyl,    benzyl, C₁-C₆alkylheteroaryl, C₁-C₆alkoxycarbonyl or    C₁-C₆alkylcarbonyl;-   R₄, R₅ and R₆ either independently of one another are hydrogen,    halogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,    C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₂-C₆alkenyl, C₂-C₆alkynyl,    unsubstituted or substituted C₃-C₈cycloalkyl, where the substituents    are selected from the group consisting of halogen and C₁-C₆alkyl, or    unsubstituted or substituted phenyl, where the substituents are    selected from the group consisting of halogen, C₁-C₆alkyl and    phenyl;-   or R₄ and R₅, together with the carbon atoms to which they are    bonded, are a five- to seven-membered, saturated or partially    unsaturated heterocyclic ring having 1 or 2 heteroatoms from the    group consisting of nitrogen, oxygen and sulphur;-   R₇ is halogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,    halo-C₁-C₆alkoxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₂-C₆alkenyl,    C₂-C₆alkynyl; aryl, phenylacetylenyl or heteroaryl, in each case    unsubstituted or mono- or polysubstituted, where the substituents    are in each case selected from the group consisting of halogen,    nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,    halo-C₁-C₆alkoxy, and can in each case be identical or different if    their number is greater than 1;-   R₈ is aryl which is unsubstituted or mono- to pentasubstituted,    where the substituents are selected from the group consisting of    halogen, nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy and    halo-C₁-C₆alkoxy, and can be identical or different if their number    is greater than 1;-   X is O, S, S(O) or S(O)₂; and-   n is 0 or 1;-   and, if appropriate, E/Z isomers, E/Z isomer mixtures and/or    tautomers, in each case in free form or in salt form;-   a process for preparation and the use of these compounds, their    isomers and tautomers; starting compounds for the preparation of the    compounds of the formula (I); pesticides whose active compound is    selected from the compounds of the formula (I) and their tautomers;    and a process for the control of plant-injurious insects and    representatives of the order Acarina, and of endo- and    ectoparasites, in particular helminths, in and on warm-blooded    agricultural and domestic animals, using these compositions.

Substituted aminoacetonitrile compounds having pesticidal action aredescribed in the literature. The active compounds actually disclosedthere however, cannot always fulfil the requirements with respect topotency and spectrum of action. There is thus a need for activecompounds having improved pesticidal properties. It has now been foundthat the compounds of the formula (I) according to the invention haveoutstanding pesticidal properties, in particular against endo- andectoparasites in and on agricultural and domestic animals and plants.

Some compounds of formula (I) may be in the form of tautomers. Thecompounds of formula (I) are therefore to be understood hereinbefore andhereinafter as including corresponding tautomers, where appropriate,even if the latter are not specifically mentioned in each case.

The compounds of formula (I) and, where appropriate, tautomers thereofare capable of forming salts, for example acid addition salts. Thoseacid addition salts are formed, for example, with strong inorganicacids, such as mineral acids, e.g. sulfuric acid, a phosphoric acid or ahydrohalic acid, with strong organic carboxylic acids, such asunsubstituted or substituted, e.g. halo-substituted,C₁-C₄alkanecarboxylic acids, e.g. acetic acid, saturated or unsaturateddicarboxylic acids, e.g. oxalic, malonic, maleic, fumaric and phthalicacid, hydroxycarboxylic acids, e.g. ascorbic, lactic, malic, tartaricand citric acid, or benzoic acid, or with organic sulfonic acids, suchas unsubstituted or substituted, e.g. halo-substituted, C₁-C₄alkane- oraryl-sulfonic acids, e.g. methane- or p-toluene-sulfonic acid.Furthermore, compounds of formula (I) having at least one acid group arecapable of forming salts with bases. Suitable salts with bases are, forexample, metal salts, such as alkali metal and alkaline earth metalsalts, e.g. sodium, potassium and magnesium salts, and salts withammonia or an organic amine, such as morpholine, piperidine,pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-,diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- ortri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine. Inaddition, corresponding internal salts may optionally also be formed.Preference is given, firstly, to the free form. Among the salts ofcompounds of formula (I) preference is given to agrochemicallyadvantageous salts. The free compounds of formula (I) and salts thereofare to be understood hereinbefore and hereinafter as including, whereappropriate, both the corresponding salts and the free compounds offormula (I), respectively. The same is correspondingly true fortautomers of compounds of formula (I) and salts thereof.

The general terms used hereinbefore and hereinafter have the followingmeanings, unless defined otherwise.

Aryl is phenyl or naphthyl.

Heteroaryl is pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl,furanyl, pyrryl, pyrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl,thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl,indolyl or indazolyl, preferably pyridyl, pyrimidyl, s-triazinyl or1,2,4-triazinyl, in particular pyridyl or pyrimidyl.

Alkyl—as a group per se and as a structural element of other groups andcompounds, such as of haloalkyl, alkoxy and alkylthio,—is, in each casetaking into account the number of the carbon atoms included from case tocase in the corresponding group or compound, either straight-chain, thatis methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, orbranched, e.g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl,neopentyl or isohexyl.

Alkenyl—as a group per se and as a structural element of other groupsand compounds—is, in each case taking into account the number of thecarbon atoms and conjugated or isolated double bonds included from caseto case in the corresponding group or compound, either straight-chain,e.g. allyl, 2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1,3-hexadienylor 1,3-octadienyl, or branched, e.g. isopropenyl, isobutenyl, isoprenyl,tert-pentenyl, isohexenyl, isoheptenyl or isooctenyl.

Alkynyl—as a group per se and as a structural element of other groupsand compounds—is, in each case taking into account the number of thecarbon atoms and conjugated or isolated double bonds included from caseto case in the corresponding group or compound, either straight-chain,e.g. propargyl, 2-butynyl, 3-pentynyl, 1-hexynyl, 1-heptynyl,3-hexen-1-ynyl, or 1,5-heptadien-3-ynyl, or branched, e.g.3-methylbut-1-ynyl, 4-ethylpent-1-ynyl, 4-methylhex-2-ynyl or2-methylhept-3-ynyl.

Cycloalkyl—as a group per se and as a structural element of other groupsand compounds, such as of halocycloalkyl—is, in each case taking intoaccount the number of the carbon atoms included from case to case in thecorresponding group or compound, cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl or cyclooctyl.

Halogen—as a group per se and as a structural element of other groupsand compounds—such as of haloalkyl, haloalkoxy and haloalkylthio—isfluorine, chlorine, bromine or iodine, in particular fluorine, chlorineor bromine, especially fluorine or chlorine.

Halogen-substituted carbon-containing groups and compounds, such ashaloalkyl, halo-alkoxy or haloalkylthio, can be partially halogenated orperhalogenated, it being possible in the case of polysubstitution forthe halogen substituents to be identical or different. Examples ofhaloalkyl—as a group per se and as a structural element of other groupsand compounds—such as of haloalkoxy, or haloalkylthio, are methyl whichis mono- to trisubstituted by fluorine, chlorine and/or bromine, such asCHF₂ or CF₃; ethyl which is mono- to pentasubstituted by fluorine,chlorine and/or bromine, such as CH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂,CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂, CF₂CHClF, CH₂CHBrF or CClFCHClF; propyl orisopropyl which is one mono- to heptasubstituted by fluorine, chlorineand/or bromine, such as CH₂CHBrCH₂Br, CF₂CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂;butyl or one of its isomers which is mono- to nonasubstituted byfluorine, chlorine and/or bromine, such as CF(CF₃)CHFCF₃ orCH₂(CF₂)₂CF₃; pentyl or one of its isomers which is mono- toundecasubstituted by fluorine, chlorine and/or bromine, such asCF(CF₃)(CHF)₂CF₃ or CH₂(CF₂)CF₃; and hexyl or one of its isomers whichis mono- to tridecasubstituted by fluorine, chlorine and/or bromine,such as (CH₂)₄CHBrCH₂Br, CF₂(CHF)₄CF₃, CH₂(CF₂)₄CF₃ or C(CF₃)₂(CHF)₂CF₃.

Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms.Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy,isobutoxy, sec-butoxy and tert-butoxy, and the isomers pentyloxy andhexyloxy; preferably methoxy and ethoxy. Haloalkoxy groups preferablyhave a chain length of 1 to 6 carbon atoms. Haloalkoxy is, for example,fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,1,1,2,2-tetrafluoroethoxy, 2-fluoro-ethoxy, 2-chloroethoxy,2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferablydifluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

Alkylthio groups preferably have a chain length of 1 to 6 carbon atoms.Alkylthio is, for example, methylthio, ethylthio, propylthio,isopropylthio, n-butylthio, isobutylthio, sec-butylthio ortert-butylthio, preferably methylthio and ethylthio.

Preferred embodiments within the context of the invention, taking intoaccount the above-mentioned proviso, are:

-   (1) a compound of the formula (I), in which R₁ is aryl which is    unsubstituted or mono- to pentasubstituted by R₇, where the    substitutents in each case can be identical or different if their    number is greater than 1; particularly aryl which is mono- to    trisubstituted by R₇, where the substituents in each case can be    identical or different if their number is greater than 1;-   (2) a compound of the formula (I), in which R₂ is C₁-C₆alkyl,    halo-C₁-C₆alkyl, aryl or heteroaryl which is in each case    unsubstituted or mono- to polysubstituted by R₇, where the    substituents can in each case be identical or different if their    number is greater than 1; particularly C₁-C₆alkyl, halo-C₁-C₆alkyl    or aryl which is unsubstituted or mono- to pentasubstituted by R₇,    where the substituents can be identical or different if their number    is greater than 1; very particularly aryl which is unsubstituted or    mono- to trisubstituted by R₇, where the substituents can be    identical or different if their number is greater than 1;-   (3) a compound of the formula (I), in which R₃ is hydrogen or    C₁-C₆alkyl; particularly hydrogen or C₁-C₄alkyl; very particularly    hydrogen;-   (4) a compound of the formula (I), in which R₄, R₅ and R₆    independently of one another are hydrogen, C₁-C₆alkyl,    halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy, C₂-C₆alkenyl,    C₂-C₆-alkynyl, C₃-C₆cycloalkyl; particularly hydrogen, C₁-C₄alkyl,    halo-C₁-C₄alkyl or C₃-C₆cycloalkyl; very particularly hydrogen or    C₁-C₂alkyl.-   (5) a compound of the formula (I), in which R₇ is halogen,    C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄-alkoxy, halo-C₁-C₄alkoxy; aryl or    phenylacetylenyl, in each case unsubstituted or mono- or    polysubstituted, where the substituents are selected from the group    consisting of halogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,    halo-C₁-C₆alkoxy, and can in each case be identical or different if    their number is greater than 1; particularly halogen, C₁-C₂alkyl,    halo-C₁-C₂alkyl, C₁-C₂alkoxy, halo-C₁-C₂alkoxy; very particularly    halogen or halo-C₁-C₂alkyl;-   (6) a compound of the formula (I), in which R₈ is unsubstituted or    mono- to trisubstituted aryl, where the substituents are selected    from the group consisting of halogen, C₁-C₄alkyl, halo-C₁-C₄alkyl,    C₁-C₄alkoxy and halo-C₁-C₄alkoxy, and can be identical or different    if their number is greater than 1; particularly mono- to    trisubstituted aryl, where the substituents are selected from the    group consisting of halogen, C₁-C₂alkyl, halo-C₁-C₂alkyl, and    halo-C₁-C₂alkoxy, and can be identical or different if their number    is greater than 1; very particularly mono- or disubstituted aryl,    where the substituents are selected from the group consisting of    halogen and halo-C₁-C₂alkyl, and can be identical or different if    their number is greater than 1;-   (7) a compound of the formula (I), in which X is O or S;    particularly 0;-   (8) a compound of the formula (1), in which n is 1;-   (9) a compound of the formula (1), in which R₁ is aryl which is    unsubstituted or mono- or pentasubstituted by R₇, where the    substituents can in each case be identical or different if their    number is greater than 1; R₂ is C₁-C₆alkyl, halo-C₁-C₆alkyl, aryl or    heteroaryl, in each case unsubstituted or mono- or polysubstituted    by R₇, where the substituents can in each case be identical or    different if their number is greater than 1; R₃ is hydrogen or    C₁-C₆alkyl; R₄, R₅ and R₆ independently of one another are hydrogen,    C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,    C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl; R₇ is halogen,    C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy, halo-C₁-C₄alkoxy, aryl or    phenylacetylenyl, in each case unsubstituted or mono- or    polysubstituted, where the substituents are selected from the group    consisting of halogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,    halo-C₁-C₆alkoxy, and in each case can be identical or different if    their number is greater than 1; R₈ is unsubstituted or mono- to    trisubstituted aryl, where the substituents are selected from the    group consisting of halogen, C₁-C₄alkyl, halo-C₁-C₄alkyl,    C₁-C₄alkoxy and halo-C₁-C₄alkoxy, and can be identical or different    if their number is greater than 1; X is O or S; and n is 1;-   (10) a compound of the formula (1), in which R₁ is aryl which is    mono- or trisubstituted by R₇, where the substituents can in each    case be identical or different if their number is greater than 1; R₂    is C₁-C₆alkyl, halo-C₁-C₆alkyl or aryl which is unsubstituted or    mono- to pentasubstituted by R₇, where the substituents can be    identical or different if their number is greater than 1; R₃ is    hydrogen or C₁-C₄alkyl; R₄, R₅ and R₆ independently of one another    are hydrogen, C₁-C₄alkyl, halo-C₁-C₄alkyl or C₃-C₆cycloalkyl; R₇ is    halogen, C₁-C₂alkyl, halo-C₁-C₂alkyl, C₁-C₂alkoxy or    halo-C₁-C₂alkoxy; R₈ is mono- to trisubstituted aryl, where the    substituents are selected from the group consisting of halogen,    C₁-C₂alkyl, halo-C₁-C₂alkyl, and halo-C₁-C₂alkoxy, and can be    identical or different if their number is greater than 1; X is O;    and n is 1;-   (11) a compound of the formula (I), in which R₁ is aryl which is    mono- to trisubstituted by R₇, where the substituents can in each    case be identical or different if their number is greater than 1; R₂    is aryl which is unsubstituted or mono- to trisubstituted by R₇,    where the substituents can in each case be identical or different if    their number is greater than 1; R₃ is hydrogen; R₄, R₅ and R₆    independently of one another are hydrogen or C₁-C₂alkyl; R₇ is    halogen or halo-C₁-C₂alkyl; R₈ is mono- or disubstituted aryl, where    the substituents are selected from the group consisting of halogen    and halo-C₁-C₂alkyl, and can be identical or different if their    number is greater than 1; X is 0; and n is 1.

Particularly preferred compounds of the formula (I) for the purposes ofthe invention are those listed in tables 1 and 2 and very particularlypreferably the compounds of the formula (I) mentioned in the synthesisexamples.

A further subject of the invention is the process for the preparation ofthe compounds of the formula (I), in each case in free form or in saltform, characterized in that a compound of the formula

which is known or can be prepared in analogy to corresponding knowncompounds and in which R₁, R₃, R₄, R₅, R₆, X and n are as defined forthe formula (I), is reacted with a compound of the formula

which is known or can be prepared in analogy to corresponding knowncompounds and in which R₂ is as defined for the formula (I) and Q is aleaving group, if appropriate in the presence of a basic catalyst, andin each case, if desired, a compound of the formula (I), in each case infree form or in salt form, obtainable according to the process or Inanother manner, is converted into another compound of the formula (I), amixture of isomers obtainable according to the process is separated andthe desired isomer is isolated and/or a free compound of the formula (I)obtainable according to the process is converted into a salt or a saltof a compound of the formula (I) obtainable according to the process isconverted into the free compound of the formula (I) or into anothersalt.

For starting materials mentioned above and below, it applies withrespect to their salts that what has been said above for salts ofcompounds of the formula (I) applies in an analogous manner.

The reactants can be reacted with one another as such, that is withoutaddition of a solvent or diluent, e.g. In the melt. Usually, however,the addition of an inert solvent or diluent or of a mixture thereof isadvantageous. Examples of such solvents or diluents which may bementioned are: aromatic, aliphatic and alicyclic hydrocarbons andhalogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene,tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether,hexane, cyclohexane, dichloromethane, trichloromethane,tetrachloromethane, dichloroethane, trichloroethene ortetrachloroethene; ethers, such as diethyl ether, dipropyl ether,diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether, ethyleneglycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran ordioxane; ketones, such as acetone, methyl ethyl ketone or methylisobutyl ketone; amides, such as N,N-dimethylformamide,N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone orhexamethylphosphoramide; nitriles, such as acetonitrile orpropionitrile; and sulphoxides, such as dimethyl sulphoxide.

Preferred leaving groups are halogens, in particular chlorine.

Suitable bases for facilitating the reaction are, for example, alkalimetal or alkaline earth metal hydroxides, hydrides, amides, alkoxides,acetates, carbonates, dialkylamides or alkylsilylamides, alkylamines,alkylenediamines, free or N-alkylated, unsaturated or saturated,cycloalkylamines, basic heterocycles, ammonium hydroxides, andcarbocyclic amines.

Examples which may be mentioned are sodium hydroxide, hydride, amide,methoxide, acetate, carbonate, potassium t-butoxide, hydroxide,carbonate, hydride, lithium diisopropylamide, potassiumbis(trimethylsilyl)amide, calcium hydride, triethylamine,diisopropylamine, triethylenediamine, cyclohexylamine,N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine,4-(N,N-dlmethylamino)pyridine, quinuclidine, N-methylmorphollne,benzyltrimethylammonium hydroxide, and1,5-diazabicyclo[5.4.0]undec-5-ene (DBU).

The reaction is advantageously carried out in a temperature range fromapproximately 0° C. to approximately +150° C., preferably fromapproximately 20° C. to approximately +100° C.

A further subject of the invention is the process for the preparation ofthe compounds of the formula (II), in each case in free form or in saltform, for example characterized in that a compound of the formula

which is known or can be prepared in analogy to corresponding knowncompounds and in which R₁, R₄, R₅, R₆, X and n are as defined for theformula (I), is reacted with an inorganic or organic cyanide and acompound of the formula R₃—NH₂, which is known or can be prepared inanalogy to corresponding known compounds and in which R₃ is as definedfor the formula (I), and in each case, if desired, a compound of theformula (II), in each case in free form or in salt form, obtainableaccording to the invention or in another manner, is converted intoanother compound of the formula (II), a mixture of isomers obtainableaccording to the process is separated and the desired isomer is isolatedand/or a free compound of the formula (II) obtainable according to theprocess is converted into a salt or a salt of a compound of the formula(II) obtainable according to the process is converted into the freecompound of the formula (II) or into another salt.

Suitable cyanides are sodium cyanide, potassium cyanide, trimethylsilylcyanide and acetone cyanohydrin.

Compounds of formula (I) obtainable in accordance with the process or byanother method can be converted in a manner known per se into differentcompounds of formula (I) by replacing one or more substituents of thestarting compound of formula (I) by (an)other substituent(s) accordingto the invention in customary manner.

Depending upon the reaction conditions and starting materials selectedas suitable in each case, it is possible in a reaction step to replaceonly one substituent by another substituent according to the inventionor it is possible in the same reaction step to replace a plurality ofsubstituents by other substituents according to the invention.

Salts of compounds of formula (I) can be prepared in a manner known perse. For example, acid addition salts of compounds of formula (I) areobtained by treatment with a suitable acid or a suitable ion exchangereagent and salts with bases are obtained by treatment with a suitablebase or a suitable ion exchange reagent.

Salts of compounds of formula (I) can be converted in customary mannerinto the free compounds of formula (I); acid addition salts can beconverted, for example, by treatment with a suitable basic medium or asuitable ion exchange reagent and salts with bases, for example, bytreatment with a suitable acid or a suitable ion exchange reagent.

Salts of compounds of formula (I) can be converted into different saltsof compounds of formula (I) in a manner known per se; for example acidaddition salts can be converted into different acid addition salts, forexample by treatment of a salt of an inorganic acid, such as ahydrochloride, with a suitable metal salt, such as a sodium, barium orsilver salt, of an acid, for example with silver acetate, in a suitablesolvent in which an inorganic salt being formed, for example silverchloride, is insoluble and is therefore precipitated out from thereaction mixture.

Depending upon the procedure and/or the reaction conditions, thecompounds of formula (I) having salt-forming properties can be obtainedin free form or in the form of salts.

The compounds of formula (I) can also be obtained in the form of theirhydrates and/or can include other solvents, for example any solvent thatmay have been used for the crystallisation of compounds in solid form.

The compounds of formulae (I) and (II) may be in the form of one of thepossible isomers or in the form of a mixture thereof, for exampledepending upon the number of asymmetric carbon atoms and the absoluteand relative configuration thereof, in the form of pure isomers, such asantipodes and/or diastereoisomers, or in the form of mixtures ofisomers, such as mixtures of enantiomers, for example racemates,mixtures of diastereoisomers or mixtures of racemates; the inventionrelates both to the pure isomers and to all possible mixtures of isomersand this is to be understood accordingly hereinbefore and hereinafter,even when stereochemical details are not specifically mentioned in eachcase.

Mixtures of diastereoisomers and mixtures of racemates of compounds offormulae (I) and (II) obtainable in accordance with theprocess—depending upon the starting materials and procedures chosen—orby other means can be separated into the pure diastereoisomers orracemates in known manner on the basis of the physico-chemicaldifferences between the constituents, for example by fractionalcrystallisation, distillation and/or chromatography.

Mixtures of enantiomers or racemates so obtainable can be separated intothe optical antipodes by known methods, for example by recrystallisationfrom an optically active solvent, by chromatography on chiraladsorbents, for example high-pressure liquid chromatography (HPLC) onacetyl cellulose, with the aid of suitable microorganisms, by cleavagewith specific immobilised enzymes, or via the formation of inclusioncompounds, for example using chiral crown ethers, in which case only oneenantiomer is complexed.

Pure diastereoisomers and enantiomers can be obtained not only byseparation of corresponding mixtures of isomers but also, according tothe invention, by generally known methods of diastereoselective orenantioselective synthesis, for example by carrying out the processaccording to the invention with starting materials that have appropriatestereochemistry.

It is advantageous to isolate or synthesise whichever isomer, forexample enantiomer, or mixture of isomers, for example mixture ofenantiomers, is biologically more active, insofar as the individualcomponents have different biological activity.

In the process of the present invention there are preferably used thosestarting materials and intermediates which result in the compounds offormula (I) described at the beginning as being especially valuable.

The invention relates especially to the preparation process described inthe Example.

The invention relates also to the novel starting materials andintermediates that are used according to the invention in thepreparation of compounds of formula (I), to their use and to processesfor the preparation thereof.

In the area of pest control, the compounds of formula (I) according tothe invention are active ingredients exhibiting valuable preventiveand/or curative activity with a very advantageous biocidal spectrum,even at low rates of concentration, while being well tolerated bywarm-blooded organisms, fish and plants. The compounds are especiallysuitable for use in the area of controlling endo- and ecto-parasites ofanimals and plant-destructive insects and representatives of the orderAcarina. The active ingredients according to the invention are effectiveagainst all or individual development stages of normally sensitiveanimal pests, but also of resistant animal pests, such as insects andrepresentatives of the order Acarina. The pesticidal activity of theactive ingredients according to the invention may manifest itselfdirectly, i.e. In the mortality of the pests, which occurs immediatelyor only after some time, for example during moulting, or indirectly, forexample in reduced oviposition and/or hatching rate, good activitycorresponding to a mortality of at least 50 to 60%. The compounds offormula (I) are especially distinguished by an unusually long durationof action.

The said animal pests of plants include those mentioned in EuropeanPatent Application EP-A-736 252, page 5, line 55 to page 6, line 55. Thepests mentioned therein are therefore included by reference in thesubject matter of the present invention.

The compounds of formula (I) can also be used against pests affectinghygiene, especially of the order Diptera with the familiesSarcophagidae, Anophilidae and Culicidae; and of the orders Orthoptera,Dictyoptera (e.g. the family Blattidae) and Hymenoptera (e.g. the familyFormicidae).

The compounds of formula (I) also have long-lasting activity in the caseof mites and insects that are parasites of plants. In the case of spidermites of the order Acarina, they are effective against eggs, nymphs andadults of Tetranychidae (Tetranychus spp. and Panonychus spp.).

They possess a high degree of activity in sucking insects of the orderHomoptera, especially against pests of the families Aphididae,Delphacidae, Cicadellidae, Psyllidae, Loccidae, Diaspididae andEriophydidae (e.g. rust mite on citrus fruit); of the orders Hemiptera,Heteroptera and Thysanoptera, and in phytophagous insects of the ordersLepidoptera, Coleoptera, Diptera and Orthoptera.

They are also suitable as a soil insecticide against pests in the soil.

The compounds according to the invention can be used to control, i.e. toinhibit or destroy, pests of the mentioned type occurring especially onplants, more especially on useful plants and ornamentals in agriculture,in horticulture and in forestry, or on parts of such plants, such as thefruits, blossoms, leaves, stems, tubers or roots, while in some casesparts of plants that grow later are still protected against those pests.

The compounds of formula (I) are therefore effective against alldevelopment stages of sucking and phytophagous insects on crops such ascereals, e.g. wheat, barley, rye, oats, rice, maize and sorghum; beet,such as sugar beet and fodder beet; fruit, e.g. pomes, stone fruit andsoft fruit, such as apples, pears, plums, peaches, almonds, cherries andberries, e.g. strawberries, raspberries and blackberries; leguminousplants, such as beans, lentils, peas and soybeans; oil plants, such asrape, mustard, poppy, olives, sunflowers, coconut, castor oil, cocoa andgroundnuts; cucurbitaceae, such as marrows, cucumbers and melons; fibreplants, such as cotton, flax, hemp and jute; citrus fruits, such asoranges, lemons, grapefruit and mandarins; vegetables, such as spinach,lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes andpaprika; lauraceae, such as avocado, cinnamon and camphor; and tobacco,nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas,natural rubber plants and ornamentals.

The compounds of formula (I) are also effective against plant-nematodesof the species Meloidogyne, Heterodera, Pratylenchus, Ditylenchus,Radopholus, Rizoglyphus and others.

In the context of the present invention, ectoparasites occurring asparasites on warm-blooded organisms are understood to mean especiallyinsects, mites and ticks. Included are insects of the orders:Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera,Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera,Psocoptera and Hymenoptera. Special mention may be made, however, ofectoparasites that trouble humans and animals and transmit pathogens,for example flies, such as Musca domestica, Musca vetustissima, Muscaautumnalis, Fannia canicularis, Sarcophaga camaria, Lucilia cuprina,Hypoderma bovis, Hypoderma lineatum, Chrysomyia chloropyga, Dermatobiahominis, Cochliomyla hominivorax, Gasterophilus intestinalis, Oestrusovis, Stomoxys calcitrans, Haematobia irritans and midges (Nematocera),such as Culicidae, Simuliidae, Psychodidae, and also bloodsuckingparasites, for example fleas, such as Ctenocephalides felis andCtenocephalides canis (cat and dog fleas), Xenopsylla cheopis, Pulexirritans, Dermatophilus penetrans, lice, such as Damalina ovis,Pediculus humanis, stable flies and horse flies (Tabanidae), Haematopotaspp., such as Haematopota pluvialis, Tabanidea spp., such as Tabanusnigrovittatus, Chrysopsinae spp., such as Chrysops caecutiens, tsetseflies, such as Glossinia species, biting insects, especiallycockroaches, such as Blatella germanica, Blatta orientalis, Periplanetaamericana, mites, such as Dermanyssus gallnae, Sarcoptes scabiei,Psoroptes ovis and Psorergates spp. and, not least, ticks. The latterbelong to the order Acarina. Known examples of ticks are, for example,Boophilus, Amblyomma, Anocentor, Dermacentor, Haemaphysalis, Hyalomma,Ixodes, Rhipicentor, Margaropus, Rhipicephalus, Argas, Otobius andOrnithodoros and the like, which preferentially infest warm-bloodedanimals, including farm animals, such as cows, pigs, sheep and goats,poultry, such as hens, turkeys and geese, animals bred for their fur,such as mink, fox, chinchillas, rabbits and the like, and domesticanimals, such as cats and dogs, but also humans.

In addition, the compounds of formula (I) are especially effectiveagainst helminths, among which the endoparasitic nematodes andtrematodes may be the cause of serious diseases of mammals and poultry,for example of sheep, pigs, goats, cattle, horses, donkeys, dogs, cats,guinea-pigs and ornamental birds. Typical nematodes in that indicationare: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia,Ascaris, Bunostonum, Oesophagostonum, Chabertia, Trichuris, Strongylus,Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia,Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. Among thetrematodes special mention should be made of the family of theFasciolideae, especially Fasciola hepatica. The special advantage of thecompounds of formula (I) is their efficacy against such parasites thatare resistant to benzimidazole-based active ingredients.

Certain Nematodirus, Cooperia and Oesophagostonum species attack theintestinal tract of the host animal whereas others of the speciesHaemonchus and Ostertagia parasitise in the stomach and those of thespecies Dictyocaulus parasitise in pulmonary tissue. Parasites of thefamilies Filariidae and Setariidae are found in the internal cell tissueand the organs, for example the heart, the blood vessels, the lymphvessels and the subcutaneous tissue. In this context special mentionshould be made of dog heartworm, Dirofilaria immitis. The compounds offormula (I) are highly effective against those parasites.

Furthermore, the compounds of formula (I) are suitable for controllingparasites that are pathogens of humans, among which, as typicalrepresentatives occurring in the digestive tract, mention should be madeof those of the species Ancylostoma, Necator, Ascaris, Strongyloldes,Trichinella, Capillaria, Trichuris and Enterobius. The compounds of thepresent invention are also effective against parasites of the speciesWuchereria, Brugia, Onchocerca and Loa from the family of theFilariidae, which occur in the blood, in tissue and various organs, andalso against Dracunculus and parasites of the species Strongyloides andTrichinella, which infect especially the gastrointestinal tract.

In the area of crop protection, the compounds of formula (I) are used inunmodified form or, preferably, together with the adjuvantsconventionally employed in formulation technology and can therefore beformulated in known manner e.g. into emulsifiable concentrates, directlydilutable solutions, dilute emulsions, soluble powders, granules, andalso encapsulations in polymer substances. As with the nature of thecompositions, the methods of application are selected in accordance withthe intended objectives and the prevailing circumstances.

The invention relates also to pesticides, such as emulsifiableconcentrates, suspension concentrates, directly sprayable or dilutablesolutions, coatable pastes, dilute emulsions, wettable powders, solublepowders, dispersible powders, wettable powders, dusts, granules orencapsulations in polymer substances, comprising at least one of theactive ingredients of the invention, the type of formulation beingchosen in accordance with the intended objectives and prevailingcircumstances. They are prepared in known manner, e.g. by homogeneouslymixing and/or grinding the active ingredients with extenders, forexample with solvents, solid carriers, and optionally surface-activecompounds (surfactants).

The active ingredient is used in those compositions in pure form: asolid active ingredient, for example, in a specific particle size, orpreferably together with at least one of the adjuvants customary informulation technology, such as extenders, for example solvents or solidcarriers, or surface-active compounds (surfactants).

As formulation adjuvants there are used, for example, solid carriers,solvents, stabilisers, “slow release” adjuvants, dyes and optionallysurface-active substances (surfactants). Suitable carriers and adjuvantsinclude all those substances customarily used in crop protectionproducts, especially in snail and slug control products. Suitableadjuvants, such as solvents, solid carriers, surface-active compounds,non-ionic surfactants, cationic surfactants, anionic surfactants andother adjuvants in the compositions used according to the invention,include e.g. those described in EP-A-736 252, page 7, line 51, to page8, line 39. They are included by reference in the subject matter of thepresent invention.

The compositions for use in crop protection generally comprise from 0.1to 99% by weight, especially from 0.1 to 95% by weight, of activeingredient and from 1 to 99.9% by weight, especially from 5 to 99.9% byweight, of at least one solid or liquid adjuvant, it generally beingpossible for from 0 to 25% by weight, especially from 0.1 to 20%, of thecompositions to consist of surfactants. Whereas commercial products willpreferably be formulated as concentrates, the end user will normallyemploy dilute formulations, which have much lower active ingredientconcentrations. Preferred compositions used in crop protection haveespecially the following compositions (%=% by weight): Emulsifiableconcentrates: active ingredient: 1 to 95%, preferably 5 to 20%surfactant: 1 to 30%, preferably 10 to 20% solvent: 5 to 98%, preferably70 to 85% Dusts: active ingredient: 0.1 to 10%, preferably 0.1 to 1%solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspensionconcentrates: active ingredient: 5 to 75%, preferably 10 to 50% water:94 to 24%, preferably 88 to 30% surfactant: 1 to 40%, preferably 2 to30% Wettable powders: active ingredient: 0.5 to 90%, preferably 1 to 80%surfactant: 0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 99%,preferably 15 to 98% Granules: active ingredient: 0.5 to 30%, preferably3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%

The anthelmintic compositions according to the invention for the controlof animal parasites in and on warm-blooded organisms generally comprisefrom 0.1 to 99% by weight, especially from 0.1 to 95% by weight, ofcompound of formula (I), from 99.9 to 1% by weight, especially from 99.8to 5% by weight, of a solid or liquid auxiliary, which includes from 0to 25% by weight, especially from 0.1 to 25% by weight, of a surfactant.

Preferred forms of administration for use in warm-blooded organisms forcontrolling helminths Include solutions, emulsions, suspensions(drenches), feed additives, powders, tablets including effervescenttablets, boli, capsules, micro-encapsulations and pour-on formulations,it being necessary to ensure that the formulation adjuvants arephysiologically tolerable.

Suitable solvents in the use of formulations for controlling animalparasites are, for example: alcohols, e.g. ethanol, propanol or butanol,and glycols and ethers and esters thereof, e.g. propylene glycol,dipropylene glycol ether, ethylene glycol, ethylene glycol monomethyl ormonoethyl ether, ketones, e.g. cyclohexanone, isophorone or diacetonealcohol, strong polar solvents, e.g. N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide or water, vegetable oils, e.g. rapeseedoil, castor oil, coconut oil or soybean oil, and also, whereappropriate, silicone oils.

Suitable binders for tablets and boli are chemically modified naturalpolymeric substances soluble in water or in alcohol, for example starch,cellulose or protein derivatives (e.g. methylcellulose,carboxymethylcellulose, ethyl hydroxyethylcellulose, proteins such aszein, gelatin and the like) and synthetic polymers, e.g. polyvinylalcohol, polyvinylpyrrolidone etc. Tablets also comprise fillers (e.g.starch, microcrystalline cellulose, sugar, lactose etc.), lubricants anddisintegrants.

When the anthelmintic compositions are in the form of feed concentrates,there are used as carriers, for example, performance feeds, feed grainsor protein concentrates. Such feed concentrates or compositions can alsocomprise, besides the active ingredients, auxiliaries, vitamins,antibiotics, chemotherapeutic agents or other pesticides, especiallybacteriostatics, fungistatics, coccidiostatics and also hormonepreparations, substances having an anabolic action or substances thatpromote growth, that influence the quality of meat of slaughteredanimals or that are useful in some other way for the organism. When thecompositions or the compounds of formula (I) contained therein are addeddirectly to the feed or drinking troughs, the final feed or drinkingtroughs contain the active ingredients in a concentration of preferablyfrom 0.0005 to 0.02% by weight (5-200 ppm).

The compounds of formula (I) according to the invention can be usedalone or in combination with other biocides. For example, in order toenhance the effect they can be combined with pesticides having the samedirection of action or, in order to broaden the spectrum of activity,they can be combined with substances having a different direction ofaction. It can also be of advantage to add so-called ‘repellents’. Whereit is desired to extend the spectrum of activity to endoparasites, e.g.worms, the compounds of formula (I) are advantageously combined withsubstances having endoparasiticidal properties. They can, of course,also be used in combination with anti-bacterial agents. Since thecompounds of formula (I) are “adulticides”, i.e. since they areeffective especially against the mature stages of target parasites, theaddition of pesticides which are more effective against the juvenilestages of the parasites may be very advantageous, since in this way themajor portion of those parasites that cause large-scale economic damagewill be reached, significantly contributing, moreover, to the avoidanceof the formation of resistance. Some combinations may also result insynergistic effects, that is to say the overall amount of activesubstance used can be reduced, which is desirable from an ecologicalstandpoint. Preferred groups of combination partners and especiallypreferred combination partners are mentioned hereinbelow; thecombinations may comprise, in addition to a compound of formula (I), oneor more of such partners.

Suitable mixing partners for use in crop protection and for use incontrolling endo- and ecto-parasites on warm-blooded organisms arebiocides, for example the insecticides and acaricides mentionedhereinbelow and sufficiently known to the person skilled in the artwhich have a different mechanism of action, for example chitin synthesisinhibitors, growth regulators; active ingredients that act in the samemanner as juvenile hormones; active ingredients that act as adulticides;broad-spectrum insecticides, broad-spectrum acaricides, and nematicides;and also the sufficiently known anthelmintics, and substances repellinginsects and/or Acarina, the said repellents and detachers.

Examples of suitable insecticides and acaricides are azamethiphos;chlorfenvinphos; cypermethrin, cypermethrin high-cis; cyromazine;diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil;fenoxycarb; fluazuron; furathiocarb; isazofos; jodfenphos; kinoprene;lufenuron; methacriphos; methidathion; monocrotophos; phosphamidon;profenofos; diofenolan; a substance obtainable from the Bacillusthuringiensis strain GC91 or from the strain NCTC11821; pymetrozine;bromopropylate; methoprene; disulfuton; quinalphos; tau-fluvalinate;thiocyclam; thiometon; aldicarb; azinphos-methyl; benfuracarb;bifenthrin; buprofezin; carbofuran; dibutylaminothio; cartap;chlorfluazuron; chlorpyrifos; cyfluthrin; lambda-cyhalothrin;alpha-cypermethrin; zeta-cypermethrin; deltamethrin; diflubenzuron;endosulfan; ethiofencarb; fenitrothion; fenobucarb; fenvalerate;formothion; methiocarb; heptenophos; imidacloprid; isoprocarb;methamidophos; methomyl; mevinphos; parathion; parathion-methyl;phosalone; pirimicarb; propoxur; teflubenzuron; terbufos; triazamate;fenobucarb; tebufenozide; fipronil; beta-cyfluthrin; silafluofen;fenpyroximate; pyridaben; fenazaquin; pyriproxyfen; pyrimidifen;nitenpyram; acetamiprid; avermectin B₁ (abamectin); emamectin; emamectinbenzoate; spinosad; a plant extract that is active against insects; apreparation comprising nematodes which is active against insects; apreparation obtainable from Bacillus subtilis; a preparation comprisingfungi which is active against insects; a preparation comprising viruseswhich is active against insects; chlorfenapyr; acephate; acrinathrin;alanycarb; alphamethrin; amitraz; Az 60541; azinphos A; azinphos M;azocyclotin; bendiocarb; bensultap; beta-cyfluthrin; BPMC; brofenprox;bromophos A; bufencarb; butocarboxin; butylpyridaben; cadusafos;carbaryl; carbophenothion; chloethocarb; chlorethoxyfos; chlormephos;cis-resmethrin; clocythrin; clofentezine; cyanophos; cycloprothrin;cyhexatin; demeton M; demeton S; demeton-5-methyl; dichlofenthion;dicliphos; diethion; dimethoate; dimethylvinphos; dioxathion;edifenphos; esfenvalerate; ethion; ethofenprox; ethoprophos; etrimphos;fenamiphos; fenbutatin oxide; fenbthiocarb; fenpropathrin; fenpyrad;fenthion; fluazinam; flucycloxuron; flucythrinate; flufenoxuron;flufenprox; fonophos; fosthiazate; fubfenprox; HCH; hexaflumuron;hexythiazox; IKI-220; iprobenfos; isofenphos; isoxathion; ivermectin;malathion; mecarbam; mesulfenphos; metaldehyde; metolcarb; milbemectin;moxidectin; naled; NC 184; omethoate; oxamyl; oxydemeton M; oxydeprofos;permethrin; phenthoate; phorate; phosmet; phoxim; pirimiphos M;pirimiphos E; promecarb; propaphos; prothiofos; prothoate; pyrachlophos;pyrada-phenthion; pyresmethrin; pyrethrum; tebufenozide; salithion;sebufos; sulfotep; sulprofos; tebufenpyrad; tebupirimphos; tefluthrin;temephos; terbam; tetrachlorvinphos; thiacloprid; thiafenox;thiamethoxam; thiodicarb; thiofanox; thionazin; thuringiensin;tralomethrin; triarthene; triazophos; triazuron; trichlorfon;triflumuron; trimethacarb; vamidothion; xylylcarb; YI 5301/5302;zetamethrin; DPX-MP062-indoxacarb; methoxyfenozide; bifenazate; XMC(3,5-xylyl methylcarbamate); or the fungus pathogen MetarhiziumAnisopliae. The mentioned mixing partners are very well known to personsskilled In the art. Most are described in various editions of ThePesticide Manual, The British Crop Protection Council, London, whileothers are described in various editions of The Merck Index, Merck &Co., Inc., Rahway, N.J., USA, or in the patent literature.

Examples of suitable anthelmintics that can be added to the compositionsare mentioned hereinbelow, a number of the examples thereof having, inaddition to anthelmintic activity, also an insecticidal and acaricidalactivity, some of them already being mentioned in the list above:

-   (A1) praziguantel=2-cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11    b-hexahydro-4H-pyrazino[2,1-α]isoquinoline-   (A2)    closantel=3,5-diiodo-N-[5-chloro-2-methyl-4-(a-cyano-4-chlorobenzyl)phenyl]salicylamide-   (A3)    triclabendazole=5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole-   (A4)    levamisol=L-(−)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1b]thiazole-   (A5) mebendazole=(5-benzoyl-1H-benzimidazol-2-yl)carbamic acid    methyl ester-   (A6) omphalotin=a macrocyclic fermentation product of the fungus    Omphalotus olearius described in WO 97/20857-   (A7) abamectin=avermectin B1-   (A8) ivermectin=22,23-dihydroavermectin B1-   (A9)    moxidectin=5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-milbemycin    B-   (A10)    doramectin=25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectin    Ala-   (A11) milbemectin=mixture of milbemycin A3 and milbemycin A4-   (A12) milbemycinoxim=5-oxime of milbemectin

Examples of suitable repelling substances (repellents and detachers) arefor instance:

-   (R1) DEET (N,N-diethyl-m-toluamide)-   (R2) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)-piperidine-   (R3)    cymiazol=N-2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene-2,4-xylidine

Given what has been said above, a further substantial aspect of thepresent invention relates to combination preparations for the control ofparasites on warm-blooded organisms, which combination preparationscomprise, in addition to a compound of formula (1), at least one furtheractive ingredient having the same direction of action or a differentdirection of action and at least one physiologically tolerable carrier.The present invention is not limited to two-component combinations.

The compositions according to the invention can be administered to theanimals being treated by topical, peroral, parenteral or subcutaneousmeans, the compositions being in the form of solutions, emulsions,suspensions (drenches), powders, tablets, boli, capsules and pour-onformulations.

The pour-on or spot-on method comprises applying the compound of formula(I) to a locally defined area of the skin or coat, advantageously on theback of the neck or the backbone of the animal. This is carried out, forexample, by applying a swab or spray of the pour-on or spot-onformulation to a relatively small area of the coat from where the activeingredient becomes distributed over a wide area of the coat almostautomatically as a result of the spreading constituents of theformulation assisted by the movements of the animal.

Pour-on and spot-on formulations advantageously comprise carriers thatpromote rapid distribution over the surface of the skin or in the coatof the host animal and are generally termed spreading oils. There aresuitable, for example, oily solutions; alcoholic and isopropanolicsolutions, e.g. solutions of 2-octyl-dodecanol or oleyl alcohol;solutions in esters of monocarboxylic acids, such as isopropylmyristate, isopropyl palmitate, lauric acid oxalic ester, oleic acidoleyl ester, oleic acid decyl ester, hexyl laurate, oleyl oleate, decyloleate, capric acid esters of saturated fatty alcohols of chain lengthC₁₂-C₁₈; solutions of esters of dicarboxylic acids, such as dibutylphthalate, diisopropyl isophthalate, adipic acid diisopropyl ester,di-n-butyl adipate or solutions of esters of aliphatic acids, e.g.glycols. It may be advantageous for a dispersant known from thepharmaceutical or cosmetic industry also to be present. Examples are2-pyrrolidone, 2-(N-alkyl)pyrrolidone, acetone, polyethylene glycol andits ethers and esters, propylene glycol or synthetic triglycerides.

The oily solutions include e.g. vegetable oils, such as olive oil,groundnut oil, sesame oil, pine oil, linseed oil and castor oil. Thevegetable oils may also be in epoxidised form. It is also possible touse paraffins and silicone oils.

Generally a pour-on or spot-on formulation will contain from 1 to 20% byweight of a compound of formula (I), from 0.1 to 50% by weightdispersant and from 45 to 98.9% by weight solvent.

The pour-on or spot-on method can be used especially advantageously forherd animals, such as cattle, horses, sheep and pigs, where it isdifficult or time-consuming to treat all the animals orally or viainjection. By virtue of its simplicity, this method can of course alsobe used for all other animals, including individual domestic animals andpets, and is very popular with the keepers of the animals because it canoften be carried out without the expert assistance of a veterinarysurgeon.

Whereas commercial products will preferably be formulated asconcentrates, the end user will normally employ dilute formulations.

Such formulations may also comprise further ingredients, such asstabilisers, antifoams, viscosity regulators, binders and tackifiers aswell as other active ingredients for obtaining special effects.

The present invention relates also to such anthelmintic compositionsemployed by the end user.

In each of the methods according to the invention for controlling pestsand in each of the pesticidal compositions according to the invention,the active ingredients of formula (I) can be used in any of theirspatial configurations or mixtures thereof.

The invention also encompasses a method for the prophylactic protectionof warm-blooded organisms, especially of productive livestock, domesticanimals and pets, against parasitic helminths, which method comprisesadministering to the animals the active ingredient of formula (I) oractive ingredient formulations prepared therefrom as an additive to thefeed or to the drinking troughs or in solid or liquid form orally, byinjection or parenterally. The invention also encompasses the compoundsof formula (I) according to the invention for use in one of thementioned methods.

The Examples that follow serve merely to illustrate the inventionwithout limiting the invention, the expression active ingredientdenoting one of the substances listed in the Tables.

Preferred formulations for use in the control of parasites onwarm-blooded organisms have the following compositions: (%=% by weight)

1. Granules a) b) active ingredient from Tables 1 or 2  5% 10% kaolin94% — highly disperse silicic acid  1% — attapulgite — 90%

The active ingredient is dissolved in methylene chloride and sprayedonto the carrier, and the solvent is then evaporated off in vacuo. Suchgranules can be mixed into the animal feed.

2. Granules active ingredient from Tables 1 or 2 3% polyethylene glycol(MW 200) 3% kaolin 94%(MW = molecular weight)The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coated granulesare obtained in this manner.

3. Tablets and boli I active ingredient from Tables 1 or 2 33.00%methylcellulose 0.80% highly disperse silicic acid 0.80% maize starch8.40% II crystalline lactose 22.50% maize starch 17.00% microcrystallinecellulose 16.50% magnesium stearate 1.00%I Methylcellulose is stirred into water. After the material has swelled,silicic acid is stirred in and the mixture is homogeneously suspended.The active ingredient and maize starch are mixed. The aqueous suspensionis incorporated into the resulting mixture and kneaded to a dough. Themass thereby obtained is granulated through a 12 M sieve and dried.II All 4 excipients are mixed well.III The premixes obtained according to 1 and 11 are mixed and compressedinto tablets or boli.

4. Injectable formulations A. Oily vehicle (slow release) 1. activeingredient from Tables 1 or 2 0.1-1.0 g groundnut oil ad 100 ml 2.active ingredient from Tables 1 or 2 0.1-1.0 g sesame oil ad 100 ml

Preparation: The active ingredient is dissolved in a portion of the oilwith stirring and optionally with gentle heating, and after cooling thesolution is made up to the desired volume and sterile-filtered through asuitable 0.22 micron membrane filter. B. Water-miscible solvent (mediumrate of release) active ingredient from Tables 1 or 2 0.1-1.0 g4-hydroxymethyl-1,3-dioxolane (glycerol formal) 40 g 1,2-propanediol ad100 ml an active ingredient from Table 1 0.1-1.0 g glycerol dimethylketal 40 g 1,2-propanediol ad 100 ml

Preparation: The active ingredient is dissolved in a portion of thesolvent with stirring, and the solution is made up to the desired volumeand sterile-filtered through a suitable 0.22 micron membrane filter. C.Aqueous solubilisate (rapid release) 1. active ingredient from Tables 1or 2 0.1-1.0 g polyethoxylated castor oil (40 ethylene oxide 10 g units)1,2-propanediol 20 g benzyl alcohol 1 g aqua ad inject. ad 100 ml 2.active ingredient from Tables 1 or 2 0.1-1.0 g polyethoxylated sorbitanmonooleate (20 ethylene 8 g oxide units) 4-hydroxymethyl-1,3-dioxolane(glycerol formal) 20 g benzyl alcohol 1 g aqua ad inject. ad 100 mlPreparation: The active ingredient is dissolved in the solvents and thesurfactant, and the solution is made up to the desired volume withwater. Sterile-filtration is then carried out through a suitablemembrane filter of 0.22 micron pore diameter.

5. Pour-on A. active ingredient from Tables 1 or 2 5 g isopropylmyristate 10 g isopropanol ad 100 ml B. active ingredient from Tables 1or 2 2 g hexyl laurate 5 g medium-chain triglycerides 15 g ethanol ad100 ml C. active ingredient from Tables 1 or 2 2 g oleyl oleate 5 gN-methyl-pyrrolidone 40 g isopropanol ad 100 ml

The aqueous systems may preferably be used also for oral and/orintraruminal administration.

The compositions may also comprise further ingredients such asstabilisers, e.g. vegetable oils and epoxidised vegetable oils(epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, e.g.silicone oil, preservatives, viscosity regulators, binders, tackifiersand fertilisers as well as other active ingredients for obtainingspecial effects.

It is also possible to add to the described compositions furtherbiologically active substances or additives that have neutral behaviourtowards the compounds of formula (I) and have no adverse effect on thehost animal to be treated, and also mineral salts or vitamins.

The compositions according to the invention are prepared in knownmanner, in the absence of adjuvants, for example by grinding, sievingand/or compressing a solid active ingredient or mixture of activeingredients, for example to a specific particle size, or in the presenceof at least one adjuvant, for example by intimately mixing and/orgrinding the active ingredient or mixture of active ingredients with theadjuvant(s). The invention relates also to those processes for thepreparation of the compositions according to the invention and to theuse of the compounds of the formula (I) in the preparation of thosecompositions.

The invention relates also to the methods of application of thecompositions, i.e. the methods of controlling pests of the mentionedtype, such as spraying, atomising, dusting, coating, dressing,scattering or pouring, which are selected in accordance with theintended objectives and prevailing circumstances, and to the use of thecompositions for controlling pests of the mentioned type. Typical ratesof concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500ppm, of active ingredient. The rates of application per hectare aregenerally from 1 to 2000 g of active ingredient per hectare, especiallyfrom 10 to 1000 g/ha, preferably from 20 to 600 g/ha.

A preferred method of application in the area of crop protection isapplication to the foliage of the plants (foliar application), thenumber of applications and the rate of application depending on the riskof infestation by the pest in question. However, the active ingredientcan also penetrate the plants through the roots (systemic action) if thelocus of the plants is impregnated with a liquid formulation or if theactive ingredient is incorporated in solid form into the locus of theplants, for example into the soil, e.g. in granular form (soilapplication). In paddy rice crops, such granules may be applied inmetered amounts to the flooded rice field.

The compositions according to the invention are also suitable forprotecting plant propagation material, including genetically modifiedpropagation material, e.g. seed material, such as fruit, tubers orgrains, or plant cuttings, from animal pests. The propagation materialcan be treated with the formulation before planting: seed, for example,can be dressed before being sown. The compounds according to theinvention can also be applied to grains (coating), either byimpregnating the grains with a liquid formulation or by coating themwith a solid formulation. The formulation can also be applied to theplanting site when the propagation material is being planted, forexample to the seed furrow during sowing. The invention relates also tothose methods of treating plant propagation material and to the plantpropagation material thus treated.

The following Examples serve to illustrate the invention. They do notlimit the invention. The symbol ‘h’ stands for ‘hour’.

PREPARATION EXAMPLES Preparation ofN-(1-cyano-1-[2,3-dichlorophenoxymethyl]ethyl)-C-phenylmethanesulphonamide

a) A mixture of 5 g of 2,3-dichlorophenol, 4 g of 2-chloroacetone, 4.7 gof anhydrous potassium carbonate and 450 mg of potassium iodide isrefluxed in 50 ml of acetone for 6 h, then cooled to room temperatureand filtered. The filtrate is evaporated.1-(2,3-Dichloro-phenoxy)acetone is obtained in this way.

b) 6.5 g of 1-(2,3-dichlorophenoxy)acetone, 1.76 g of sodium cyanide and2.4 g of ammonium chloride are added to a solution of 30 ml of 25%ammonia and the mixture is stirred at room temperature for 24 h. Thecrude product is then extracted from the mixture using ethyl acetate,and the organic phase is separated off, washed with water and saturatedsodium chloride solution, dried using magnesium sulphate and evaporated.2-Amino-3-(2,3-dichlorophenoxy)-2-methylpropionitrile is thus obtained.

c) 5.2 g of α-toluenesulphonyl chloride are added to a mixture of 6.6 gof 2-amino-3-(2,3-dichlorophenoxy)-2-methylpropionitrile and 4.86 g ofethyldiisopropylamines in 50 ml of methylene chloride and the mixture isstirred at room temperature for 24 h. The crude product is thenextracted from the mixture with ethyl acetate, and the organic phase isseparated off, washed with aqueous sodium bicarbonate and saturatedsodium chloride solution, dried using magnesium sulphate and evaporated.The residue is purified by high-pressure column chromatography on silicagel using hexane/ethyl acetate (2:1). The title compound is thusobtained.

The substances mentioned in the table below can also be preparedanalogously to the procedures described above. The values of the meltingpoints are indicated in ° C. TABLE 1

No. R₂ n (Y) phys. Data 1.1 CH₃ 0 H 1.2 CH₃ 0 2-F 1.3 CH₃ 0 3-F 1.4 CH₃0 4-F 1.5 CH₃ 0 2-Cl 1.6 CH₃ 0 3-Cl 1.7 CH₃ 0 4-Cl 1.8 CH₃ 0 2,3-Cl₂ 1.9CH₃ 0 2,4-Cl₂ 1.10 CH₃ 0 2,5-Cl₂ 1.11 CH₃ 0 2,6-Cl₂ 1.12 CH₃ 0 3,4-Cl₂1.13 CH₃ 0 3,5-Cl₂ 1.14 CH₃ 0 3-CF₃ 1.15 CH₃ 0 4-CF₃ 1.16 CH₃ 1 H 1.17CH₃ 1 2-F 1.18 CH₃ 1 3-F 1.19 CH₃ 1 4-F 1.20 CH₃ 1 2-Cl 1.21 CH₃ 1 3-Cl1.22 CH₃ 1 4-Cl 1.23 CH₃ 1 2,3-Cl₂ 1.24 CH₃ 1 2,4-Cl₂ 1.25 CH₃ 1 2,5-Cl₂1.26 CH₃ 1 2,6-Cl₂ 1.27 CH₃ 1 3,4-Cl₂ 1.28 CH₃ 1 3,5-Cl₂ 1.29 CH₃ 13-CF₃ 1.30 CH₃ 1 4-CF₃ 1.31 C₂H₅ 0 H 1.32 C₂H₅ 0 2-F 1.33 C₂H₅ 0 3-F1.34 C₂H₅ 0 4-F 1.35 C₂H₅ 0 2-Cl 1.36 C₂H₅ 0 3-Cl 1.37 C₂H₅ 0 4-Cl 1.38C₂H₅ 0 2,3-Cl₂ 1.39 C₂H₅ 0 2,4-Cl₂ 1.40 C₂H₅ 0 2,5-Cl₂ 1.41 C₂H₅ 02,6-Cl₂ 1.42 C₂H₅ 0 3,4-Cl₂ 1.43 C₂H₅ 0 3,5-Cl₂ 1.44 C₂H₅ 0 3-CF₃ 1.45C₂H₅ 0 4-CF₃ 1.46 C₂H₅ 1 H 1.47 C₂H₅ 1 2-F 1.48 C₂H₅ 1 3-F 1.49 C₂H₅ 14-F 1.50 C₂H₅ 1 2-Cl 1.51 C₂H₅ 1 3-Cl 1.52 C₂H₅ 1 4-Cl 1.53 C₂H₅ 12,3-Cl₂ 1.54 C₂H₅ 1 2,4-Cl₂ 1.55 C₂H₅ 1 2,5-Cl₂ 1.56 C₂H₅ 1 2,6-Cl₂ 1.57C₂H₅ 1 3,4-Cl₂ 1.58 C₂H₅ 1 3,5-Cl₂ 1.59 C₂H₅ 1 3-CF₃ 1.60 C₂H₅ 1 4-CF₃1.61 n-C₃H₇ 0 H 1.62 n-C₃H₇ 0 2-F 1.63 n-C₃H₇ 0 3-F 1.64 n-C₃H₇ 0 4-F1.65 n-C₃H₇ 0 2-Cl 1.66 n-C₃H₇ 0 3-Cl 1.67 n-C₃H₇ 0 4-Cl 1.68 n-C₃H₇ 02,3-Cl₂ 1.69 n-C₃H₇ 0 2,4-Cl₂ 1.70 n-C₃H₇ 0 2,5-Cl₂ 1.71 n-C₃H₇ 02,6-Cl₂ 1.72 n-C₃H₇ 0 3,4-Cl₂ 1.73 n-C₃H₇ 0 3,5-Cl₂ 1.74 n-C₃H₇ 0 3-CF₃1.75 n-C₃H₇ 0 4-CF₃ 1.76 n-C₃H₇ 1 H 1.77 n-C₃H₇ 1 2-F 1.78 n-C₃H₇ 1 3-F1.79 n-C₃H₇ 1 4-F 1.80 n-C₃H₇ 1 2-Cl 1.81 n-C₃H₇ 1 3-Cl 1.82 n-C₃H₇ 14-Cl 1.83 n-C₃H₇ 1 2,3-Cl₂ 1.84 n-C₃H₇ 1 2,4-Cl₂ 1.85 n-C₃H₇ 1 2,5-Cl₂1.86 n-C₃H₇ 1 2,6-Cl₂ 1.87 n-C₃H₇ 1 3,4-Cl₂ 1.88 n-C₃H₇ 1 3,5-Cl₂ 1.89n-C₃H₇ 1 3-CF₃ 1.90 n-C₃H₇ 1 4-CF₃ 1.91 n-C₄H₉ 0 H 1.92 n-C₄H₉ 0 2-F1.93 n-C₄H₉ 0 3-F 1.94 n-C₄H₉ 0 4-F 1.95 n-C₄H₉ 0 2-Cl 1.96 n-C₄H₉ 03-Cl 1.97 n-C₄H₉ 0 4-Cl 1.98 n-C₄H₉ 0 2,3-Cl₂ 1.99 n-C₄H₉ 0 2,4-Cl₂1.100 n-C₄H₉ 0 2,5-Cl₂ 1.101 n-C₄H₉ 0 2,6-Cl₂ 1.102 n-C₄H₉ 0 3,4-Cl₂1.103 n-C₄H₉ 0 3,5-Cl₂ 1.104 n-C₄H₉ 0 3-CF₃ 1.105 n-C₄H₉ 0 4-CF₃ 1.106n-C₄H₉ 1 H 1.107 n-C₄H₉ 1 2-F 1.108 n-C₄H₉ 1 3-F 1.109 n-C₄H₉ 1 4-F1.110 n-C₄H₉ 1 2-Cl 1.111 n-C₄H₉ 1 3-Cl 1.112 n-C₄H₉ 1 4-Cl 1.113 n-C₄H₉1 2,3-Cl₂ 1.114 n-C₄H₉ 1 2,4-Cl₂ 1.115 n-C₄H₉ 1 2,5-Cl₂ 1.116 n-C₄H₉ 12,6-Cl₂ 1.117 n-C₄H₉ 1 3,4-Cl₂ 1.118 n-C₄H₉ 1 3,5-Cl₂ 1.119 n-C₄H₉ 13-CF₃ 1.120 n-C₄H₉ 1 4-CF₃ 1.121 CH₂C₆H₅ 0 H 1.122 CH₂C₆H₅ 0 2-F 1.123CH₂C₆H₅ 0 3-F 1.124 CH₂C₆H₅ 0 4-F 1.125 CH₂C₆H₅ 0 2-Cl 1.126 CH₂C₆H₅ 03-Cl 1.127 CH₂C₆H₅ 0 4-Cl 1.128 CH₂C₆H₅ 0 2,3-Cl₂ 1.129 CH₂C₆H₅ 02,4-Cl₂ 1.130 CH₂C₆H₅ 0 2,5-Cl₂ 1.131 CH₂C₆H₅ 0 2,6-Cl₂ 1.132 CH₂C₆H₅ 03,4-Cl₂ 1.133 CH₂C₆H₅ 0 3,5-Cl₂ 1.134 CH₂C₆H₅ 0 3-CF₃ 1.135 CH₂C₆H₅ 04-CF₃ 1.136 CH₂C₆H₅ 1 H 1.137 CH₂C₆H₅ 1 2-F 1.138 CH₂C₆H₅ 1 3-F 1.139CH₂C₆H₅ 1 4-F 1.140 CH₂C₆H₅ 1 2-Cl 1.141 CH₂C₆H₅ 1 3-Cl 1.142 CH₂C₆H₅ 14-Cl 1.143 CH₂C₆H₅ 1 2,3-Cl₂ 1.144 CH₂C₆H₅ 1 2,4-Cl₂ 1.145 CH₂C₆H₅ 12,5-Cl₂ 1.146 CH₂C₆H₅ 1 2,6-Cl₂ 1.147 CH₂C₆H₅ 1 3,4-Cl₂ 1.148 CH₂C₆H₅ 13,5-Cl₂ 1.149 CH₂C₆H₅ 1 3-CF₃ 1.150 CH₂C₆H₅ 1 4-CF₃ 1.151 C₆H₅ 0 H 1.152C₆H₅ 0 2-F 1.153 C₆H₅ 0 3-F 1.154 C₆H₅ 0 4-F 1.155 C₆H₅ 0 2-Cl 1.156C₆H₅ 0 3-Cl 1.157 C₆H₅ 0 4-Cl 1.158 C₆H₅ 0 2,3-Cl₂ 1.159 C₆H₅ 0 2,4-Cl₂1.160 C₆H₅ 0 2,5-Cl₂ 1.161 C₆H₅ 0 2,6-Cl₂ 1.162 C₆H₅ 0 3,4-Cl₂ 1.163C₆H₅ 0 3,5-Cl₂ 1.164 C₆H₅ 0 3-CF₃ 1.165 C₆H₅ 0 4-CF₃ 1.166 C₆H₅ 1 H1.167 C₆H₅ 1 2-F 1.168 C₆H₅ 1 3-F 1.169 C₆H₅ 1 4-F 1.170 C₆H₅ 1 2-Cl1.171 C₆H₅ 1 3-Cl 1.172 C₆H₅ 1 4-Cl 1.173 C₆H₅ 1 2,3-Cl₂ 1.174 C₆H₅ 12,4-Cl₂ 1.175 C₆H₅ 1 2,5-Cl₂ 1.176 C₆H₅ 1 2,6-Cl₂ 1.177 C₆H₅ 1 3,4-Cl₂1.178 C₆H₅ 1 3,5-Cl₂ 1.179 C₆H₅ 1 3-CF₃ 1.180 C₆H₅ 1 4-CF₃ 1.181C₆H₄-4-CH₃ 0 H 1.182 C₆H₄-4-CH₃ 0 2-F 1.183 C₆H₄-4-CH₃ 0 3-F 1.184C₆H₄-4-CH₃ 0 4-F 1.185 C₆H₄-4-CH₃ 0 2-Cl 1.186 C₆H₄-4-CH₃ 0 3-Cl 1.187C₆H₄-4-CH₃ 0 4-Cl 1.188 C₆H₄-4-CH₃ 0 2,3-Cl₂ 1.189 C₆H₄-4-CH₃ 0 2,4-Cl₂1.190 C₆H₄-4-CH₃ 0 2,5-Cl₂ 1.191 C₆H₄-4-CH₃ 0 2,6-Cl₂ 1.192 C₆H₄-4-CH₃ 03,4-Cl₂ 1.193 C₆H₄-4-CH₃ 0 3,5-Cl₂ 1.194 C₆H₄-4-CH₃ 0 3-CF₃ 1.195C₆H₄-4-CH₃ 0 4-CF₃ 1.196 C₆H₄-4-CH₃ 1 H 1.197 C₆H₄-4-CH₃ 1 2-F 1.198C₆H₄-4-CH₃ 1 3-F 1.199 C₆H₄-4-CH₃ 1 4-F 1.200 C₆H₄-4-CH₃ 1 2-Cl 1.201C₆H₄-4-CH₃ 1 3-Cl 1.202 C₆H₄-4-CH₃ 1 4-Cl 1.203 C₆H₄-4-CH₃ 1 2,3-Cl₂1.204 C₆H₄-4-CH₃ 1 2,4-Cl₂ 1.205 C₆H₄-4-CH₃ 1 2,5-Cl₂ 1.206 C₆H₄-4-CH₃ 12,6-Cl₂ 1.207 C₆H₄-4-CH₃ 1 3,4-Cl₂ 1.208 C₆H₄-4-CH₃ 1 3,5-Cl₂ 1.209C₆H₄-4-CH₃ 1 3-CF₃ 1.210 C₆H₄-4-CH₃ 1 4-CF₃ 1.211 C₆H₄-4-F 0 H 1.212C₆H₄-4-F 0 2-F 1.213 C₆H₄-4-F 0 3-F 1.214 C₆H₄-4-F 0 4-F 1.215 C₆H₄-4-F0 2-Cl 1.216 C₆H₄-4-F 0 3-Cl 1.217 C₆H₄-4-F 0 4-Cl 1.218 C₆H₄-4-F 02,3-Cl₂ 1.219 C₆H₄-4-F 0 2,4-Cl₂ 1.220 C₆H₄-4-F 0 2,5-Cl₂ 1.221 C₆H₄-4-F0 2,6-Cl₂ 1.222 C₆H₄-4-F 0 3,4-Cl₂ 1.223 C₆H₄-4-F 0 3,5-Cl₂ 1.224C₆H₄-4-F 0 3-CF₃ 1.225 C₆H₄-4-F 0 4-CF₃ 1.226 C₆H₄-4-F 1 H 1.227C₆H₄-4-F 1 2-F 1.228 C₆H₄-4-F 1 3-F 1.229 C₆H₄-4-F 1 4-F 1.230 C₆H₄-4-F1 2-Cl 1.231 C₆H₄-4-F 1 3-Cl 1.232 C₆H₄-4-F 1 4-Cl 1.233 C₆H₄-4-F 12,3-Cl₂ 1.234 C₆H₄-4-F 1 2,4-Cl₂ 1.235 C₆H₄-4-F 1 2,5-Cl₂ 1.236 C₆H₄-4-F1 2,6-Cl₂ 1.237 C₆H₄-4-F 1 3,4-Cl₂ 1.238 C₆H₄-4-F 1 3,5-Cl₂ 1.239C₆H₄-4-F 1 3-CF₃ 1.240 C₆H₄-4-F 1 4-CF₃ 1.241 C₆H₄-4-Cl 0 H 1.242C₆H₄-4-Cl 0 2-F 1.243 C₆H₄-4-Cl 0 3-F 1.244 C₆H₄-4-Cl 0 4-F 1.245C₆H₄-4-Cl 0 2-Cl 1.246 C₆H₄-4-Cl 0 3-Cl 1.247 C₆H₄-4-Cl 0 4-Cl 1.248C₆H₄-4-Cl 0 2,3-Cl₂ 1.249 C₆H₄-4-Cl 0 2,4-Cl₂ 1.250 C₆H₄-4-Cl 0 2,5-Cl₂1.251 C₆H₄-4-Cl 0 2,6-Cl₂ 1.252 C₆H₄-4-Cl 0 3,4-Cl₂ 1.253 C₆H₄-4-Cl 03,5-Cl₂ 1.254 C₆H₄-4-Cl 0 3-CF₃ 1.255 C₆H₄-4-Cl 0 4-CF₃ 1.256 C₆H₄-4-Cl1 H 1.257 C₆H₄-4-Cl 1 2-F 1.258 C₆H₄-4-Cl 1 3-F 1.259 C₆H₄-4-Cl 1 4-F1.260 C₆H₄-4-Cl 1 2-Cl 1.261 C₆H₄-4-Cl 1 3-Cl 1.262 C₆H₄-4-Cl 1 4-Cl1.263 C₆H₄-4-Cl 1 2,3-Cl₂ 1.264 C₆H₄-4-Cl 1 2,4-Cl₂ 1.265 C₆H₄-4-Cl 12,5-Cl₂ 1.266 C₆H₄-4-Cl 1 2,6-Cl₂ 1.267 C₆H₄-4-Cl 1 3,4-Cl₂ 1.268C₆H₄-4-Cl 1 3,5-Cl₂ 1.269 C₆H₄-4-Cl 1 3-CF₃ 1.270 C₆H₄-4-Cl 1 4-CF₃1.271 C₆H₄-4-Br 0 H 1.272 C₆H₄-4-Br 0 2-F 1.273 C₆H₄-4-Br 0 3-F 1.274C₆H₄-4-Br 0 4-F 1.275 C₆H₄-4-Br 0 2-Cl 1.276 C₆H₄-4-Br 0 3-Cl 1.277C₆H₄-4-Br 0 4-Cl 1.278 C₆H₄-4-Br 0 2,3-Cl₂ 1.279 C₆H₄-4-Br 0 2,4-Cl₂1.280 C₆H₄-4-Br 0 2,5-Cl₂ 1.281 C₆H₄-4-Br 0 2,6-Cl₂ 1.282 C₆H₄-4-Br 03,4-Cl₂ 1.283 C₆H₄-4-Br 0 3,5-Cl₂ 1.284 C₆H₄-4-Br 0 3-CF₃ 1.285C₆H₄-4-Br 0 4-CF₃ 1.286 C₆H₄-4-Br 1 H 1.287 C₆H₄-4-Br 1 2-F 1.288C₆H₄-4-Br 1 3-F 1.289 C₆H₄-4-Br 1 4-F 1.290 C₆H₄-4-Br 1 2-Cl 1.291C₆H₄-4-Br 1 3-Cl 1.292 C₆H₄-4-Br 1 4-Cl 1.293 C₆H₄-4-Br 1 2,3-Cl₂ 1.294C₆H₄-4-Br 1 2,4-Cl₂ 1.295 C₆H₄-4-Br 1 2,5-Cl₂ 1.296 C₆H₄-4-Br 1 2,6-Cl₂1.297 C₆H₄-4-Br 1 3,4-Cl₂ 1.298 C₆H₄-4-Br 1 3,5-Cl₂ 1.299 C₆H₄-4-Br 13-CF₃ 1.300 C₆H₄-4-Br 1 4-CF₃ 1.301 C₆H₄-4-OCH₃ 0 H 1.302 C₆H₄-4-OCH₃ 02-F 1.303 C₆H₄-4-OCH₃ 0 3-F 1.304 C₆H₄-4-OCH₃ 0 4-F 1.305 C₆H₄-4-OCH₃ 02-Cl 1.306 C₆H₄-4-OCH₃ 0 3-Cl 1.307 C₆H₄-4-OCH₃ 0 4-Cl 1.308 C₆H₄-4-OCH₃0 2,3-Cl₂ 1.309 C₆H₄-4-OCH₃ 0 2,4-Cl₂ 1.310 C₆H₄-4-OCH₃ 0 2,5-Cl₂ 1.311C₆H₄-4-OCH₃ 0 2,6-Cl₂ 1.312 C₆H₄-4-OCH₃ 0 3,4-Cl₂ 1.313 C₆H₄-4-OCH₃ 03,5-Cl₂ 1.314 C₆H₄-4-OCH₃ 0 3-CF₃ 1.315 C₆H₄-4-OCH₃ 0 4-CF₃ 1.316C₆H₄-4-OCH₃ 1 H 1.317 C₆H₄-4-OCH₃ 1 2-F 1.318 C₆H₄-4-OCH₃ 1 3-F 1.319C₆H₄-4-OCH₃ 1 4-F 1.320 C₆H₄-4-OCH₃ 1 2-Cl 1.321 C₆H₄-4-OCH₃ 1 3-Cl1.322 C₆H₄-4-OCH₃ 1 4-Cl 1.323 C₆H₄-4-OCH₃ 1 2,3-Cl₂ 1.324 C₆H₄-4-OCH₃ 12,4-Cl₂ 1.325 C₆H₄-4-OCH₃ 1 2,5-Cl₂ 1.326 C₆H₄-4-OCH₃ 1 2,6-Cl₂ 1.327C₆H₄-4-OCH₃ 1 3,4-Cl₂ 1.328 C₆H₄-4-OCH₃ 1 3,5-Cl₂ 1.329 C₆H₄-4-OCH₃ 13-CF₃ 1.330 C₆H₄-4-OCH₃ 1 4-CF₃ 1.331 C₆H₄-2-CF₃ 0 H 1.332 C₆H₄-2-CF₃ 02-F 1.333 C₆H₄-2-CF₃ 0 3-F 1.334 C₆H₄-2-CF₃ 0 4-F 1.335 C₆H₄-2-CF₃ 02-Cl 1.336 C₆H₄-2-CF₃ 0 3-Cl 1.337 C₆H₄-2-CF₃ 0 4-Cl 1.338 C₆H₄-2-CF₃ 02,3-Cl₂ 1.339 C₆H₄-2-CF₃ 0 2,4-Cl₂ 1.340 C₆H₄-2-CF₃ 0 2,5-Cl₂ 1.341C₆H₄-2-CF₃ 0 2,6-Cl₂ 1.342 C₆H₄-2-CF₃ 0 3,4-Cl₂ 1.343 C₆H₄-2-CF₃ 03,5-Cl₂ 1.344 C₆H₄-2-CF₃ 0 3-CF₃ 1.345 C₆H₄-2-CF₃ 0 4-CF₃ 1.346C₆H₄-2-CF₃ 1 H 1.347 C₆H₄-2-CF₃ 1 2-F 1.348 C₆H₄-2-CF₃ 1 3-F 1.349C₆H₄-2-CF₃ 1 4-F 1.350 C₆H₄-2-CF₃ 1 2-Cl 1.351 C₆H₄-2-CF₃ 1 3-Cl 1.352C₆H₄-2-CF₃ 1 4-Cl 1.353 C₆H₄-2-CF₃ 1 2,3-Cl₂ 1.354 C₆H₄-2-CF₃ 1 2,4-Cl₂1.355 C₆H₄-2-CF₃ 1 2,5-Cl₂ 1.356 C₆H₄-2-CF₃ 1 2,6-Cl₂ 1.357 C₆H₄-2-CF₃ 13,4-Cl₂ 1.358 C₆H₄-2-CF₃ 1 3,5-Cl₂ 1.359 C₆H₄-2-CF₃ 1 3-CF₃ 1.360C₆H₄-2-CF₃ 1 4-CF₃ 1.361 C₆H₄-3-CF₃ 0 H 1.362 C₆H₄-3-CF₃ 0 2-F 1.363C₆H₄-3-CF₃ 0 3-F 1.364 C₆H₄-3-CF₃ 0 4-F 1.365 C₆H₄-3-CF₃ 0 2-Cl 1.366C₆H₄-3-CF₃ 0 3-Cl 1.367 C₆H₄-3-CF₃ 0 4-Cl 1.368 C₆H₄-3-CF₃ 0 2,3-Cl₂1.369 C₆H₄-3-CF₃ 0 2,4-Cl₂ 1.370 C₆H₄-3-CF₃ 0 2,5-Cl₂ 1.371 C₆H₄-3-CF₃ 02,6-Cl₂ 1.372 C₆H₄-3-CF₃ 0 3,4-Cl₂ 1.373 C₆H₄-3-CF₃ 0 3,5-Cl₂ 1.374C₆H₄-3-CF₃ 0 3-CF₃ 1.375 C₆H₄-3-CF₃ 0 4-CF₃ 1.376 C₆H₄-3-CF₃ 1 H 1.377C₆H₄-3-CF₃ 1 2-F 1.378 C₆H₄-3-CF₃ 1 3-F 1.379 C₆H₄-3-CF₃ 1 4-F 1.380C₆H₄-3-CF₃ 1 2-Cl 1.381 C₆H₄-3-CF₃ 1 3-Cl 1.382 C₆H₄-3-CF₃ 1 4-Cl 1.383C₆H₄-3-CF₃ 1 2,3-Cl₂ 1.384 C₆H₄-3-CF₃ 1 2,4-Cl₂ 1.385 C₆H₄-3-CF₃ 12,5-Cl₂ 1.386 C₆H₄-3-CF₃ 1 2,6-Cl₂ 1.387 C₆H₄-3-CF₃ 1 3,4-Cl₂ 1.388C₆H₄-3-CF₃ 1 3,5-Cl₂ 1.389 C₆H₄-3-CF₃ 1 3-CF₃ 1.390 C₆H₄-3-CF₃ 1 4-CF₃1.391 C₆H₄-4-CF₃ 0 H 1.392 C₆H₄-4-CF₃ 0 2-F 1.393 C₆H₄-4-CF₃ 0 3-F 1.394C₆H₄-4-CF₃ 0 4-F 1.395 C₆H₄-4-CF₃ 0 2-Cl 1.396 C₆H₄-4-CF₃ 0 3-Cl 1.397C₆H₄-4-CF₃ 0 4-Cl 1.398 C₆H₄-4-CF₃ 0 2,3-Cl₂ 1.399 C₆H₄-4-CF₃ 0 2,4-Cl₂1.400 C₆H₄-4-CF₃ 0 2,5-Cl₂ 1.401 C₆H₄-4-CF₃ 0 2,6-Cl₂ 1.402 C₆H₄-4-CF₃ 03,4-Cl₂ 1.403 C₆H₄-4-CF₃ 0 3,5-Cl₂ 1.404 C₆H₄-4-CF₃ 0 3-CF₃ 1.405C₆H₄-4-CF₃ 0 4-CF₃ 1.406 C₆H₄-4-CF₃ 1 H 1.407 C₆H₄-4-CF₃ 1 2-F 1.408C₆H₄-4-CF₃ 1 3-F 1.409 C₆H₄-4-CF₃ 1 4-F 1.410 C₆H₄-4-CF₃ 1 2-Cl 1.411C₆H₄-4-CF₃ 1 3-Cl 1.412 C₆H₄-4-CF₃ 1 4-Cl 1.413 C₆H₄-4-CF₃ 1 2,3-Cl₂1.414 C₆H₄-4-CF₃ 1 2,4-Cl₂ 1.415 C₆H₄-4-CF₃ 1 2,5-Cl₂ 1.416 C₆H₄-4-CF₃ 12,6-Cl₂ 1.417 C₆H₄-4-CF₃ 1 3,4-Cl₂ 1.418 C₆H₄-4-CF₃ 1 3,5-Cl₂ 1.419C₆H₄-4-CF₃ 1 3-CF₃ 1.420 C₆H₄-4-CF₃ 1 4-CF₃ 1.421 C₆H₄-3-NO₂ 0 H 1.422C₆H₄-3-NO₂ 0 2-F 1.423 C₆H₄-3-NO₂ 0 3-F 1.424 C₆H₄-3-NO₂ 0 4-F 1.425C₆H₄-3-NO₂ 0 2-Cl 1.426 C₆H₄-3-NO₂ 0 3-Cl 1.427 C₆H₄-3-NO₂ 0 4-Cl 1.428C₆H₄-3-NO₂ 0 2,3-Cl₂ 1.429 C₆H₄-3-NO₂ 0 2,4-Cl₂ 1.430 C₆H₄-3-NO₂ 02,5-Cl₂ 1.431 C₆H₄-3-NO₂ 0 2,6-Cl₂ 1.432 C₆H₄-3-NO₂ 0 3,4-Cl₂ 1.433C₆H₄-3-NO₂ 0 3,5-Cl₂ 1.434 C₆H₄-3-NO₂ 0 3-CF₃ 1.435 C₆H₄-3-NO₂ 0 4-CF₃1.436 C₆H₄-3-NO₂ 1 H 1.437 C₆H₄-3-NO₂ 1 2-F 1.438 C₆H₄-3-NO₂ 1 3-F 1.439C₆H₄-3-NO₂ 1 4-F 1.440 C₆H₄-3-NO₂ 1 2-Cl 1.441 C₆H₄-3-NO₂ 1 3-Cl 1.442C₆H₄-3-NO₂ 1 4-Cl 1.443 C₆H₄-3-NO₂ 1 2,3-Cl₂ 1.444 C₆H₄-3-NO₂ 1 2,4-Cl₂1.445 C₆H₄-3-NO₂ 1 2,5-Cl₂ 1.446 C₆H₄-3-NO₂ 1 2,6-Cl₂ 1.447 C₆H₄-3-NO₂ 13,4-Cl₂ 1.448 C₆H₄-3-NO₂ 1 3,5-Cl₂ 1.449 C₆H₄-3-NO₂ 1 3-CF₃ 1.450C₆H₄-3-NO₂ 1 4-CF₃ 1.451 C₆H₂-2,3,4-Cl₃ 0 H 1.452 C₆H₂-2,3,4-Cl₃ 0 2-F1.453 C₆H₂-2,3,4-Cl₃ 0 3-F 1.454 C₆H₂-2,3,4-Cl₃ 0 4-F 1.455C₆H₂-2,3,4-Cl₃ 0 2-Cl 1.456 C₆H₂-2,3,4-Cl₃ 0 3-Cl 1.457 C₆H₂-2,3,4-Cl₃ 04-Cl 1.458 C₆H₂-2,3,4-Cl₃ 0 2,3-Cl₂ 1.459 C₆H₂-2,3,4-Cl₃ 0 2,4-Cl₂ 1.460C₆H₂-2,3,4-Cl₃ 0 2,5-Cl₂ 1.461 C₆H₂-2,3,4-Cl₃ 0 2,6-Cl₂ 1.462C₆H₂-2,3,4-Cl₃ 0 3,4-Cl₂ 1.463 C₆H₂-2,3,4-Cl₃ 0 3,5-Cl₂ 1.464C₆H₂-2,3,4-Cl₃ 0 3-CF₃ 1.465 C₆H₂-2,3,4-Cl₃ 0 4-CF₃ 1.466 C₆H₂-2,3,4-Cl₃1 H 1.467 C₆H₂-2,3,4-Cl₃ 1 2-F 1.468 C₆H₂-2,3,4-Cl₃ 1 3-F 1.469C₆H₂-2,3,4-Cl₃ 1 4-F 1.470 C₆H₂-2,3,4-Cl₃ 1 2-Cl 1.471 C₆H₂-2,3,4-Cl₃ 13-Cl 1.472 C₆H₂-2,3,4-Cl₃ 1 4-Cl 1.473 C₆H₂-2,3,4-Cl₃ 1 2,3-Cl₂ 1.474C₆H₂-2,3,4-Cl₃ 1 2,4-Cl₂ 1.475 C₆H₂-2,3,4-Cl₃ 1 2,5-Cl₂ 1.476C₆H₂-2,3,4-Cl₃ 1 2,6-Cl₂ 1.477 C₆H₂-2,3,4-Cl₃ 1 3,4-Cl₂ 1.478C₆H₂-2,3,4-Cl₃ 1 3,5-Cl₂ 1.479 C₆H₂-2,3,4-Cl₃ 1 3-CF₃ 1.480C₆H₂-2,3,4-Cl₃ 1 4-CF₃ 1.481 C₆H₂-2,4,5-Cl₃ 0 H 1.482 C₆H₂-2,4,5-Cl₃ 02-F 1.483 C₆H₂-2,4,5-Cl₃ 0 3-F 1.484 C₆H₂-2,4,5-Cl₃ 0 4-F 1.485C₆H₂-2,4,5-Cl₃ 0 2-Cl 1.486 C₆H₂-2,4,5-Cl₃ 0 3-Cl 1.487 C₆H₂-2,4,5-Cl₃ 04-Cl 1.488 C₆H₂-2,4,5-Cl₃ 0 2,3-Cl₂ 1.489 C₆H₂-2,4,5-Cl₃ 0 2,4-Cl₂ 1.490C₆H₂-2,4,5-Cl₃ 0 2,5-Cl₂ 1.491 C₆H₂-2,4,5-Cl₃ 0 2,6-Cl₂ 1.492C₆H₂-2,4,5-Cl₃ 0 3,4-Cl₂ 1.493 C₆H₂-2,4,5-Cl₃ 0 3,5-Cl₂ 1.494C₆H₂-2,4,5-Cl₃ 0 3-CF₃ 1.495 C₆H₂-2,4,5-Cl₃ 0 4-CF₃ 1.496 C₆H₂-2,4,5-Cl₃1 H 1.497 C₆H₂-2,4,5-Cl₃ 1 2-F 1.498 C₆H₂-2,4,5-Cl₃ 1 3-F 1.499C₆H₂-2,4,5-Cl₃ 1 4-F 1.500 C₆H₂-2,4,5-Cl₃ 1 2-Cl 1.501 C₆H₂-2,4,5-Cl₃ 13-Cl 1.502 C₆H₂-2,4,5-Cl₃ 1 4-Cl 1.503 C₆H₂-2,4,5-Cl₃ 1 2,3-Cl₂ 1.504C₆H₂-2,4,5-Cl₃ 1 2,4-Cl₂ 1.505 C₆H₂-2,4,5-Cl₃ 1 2,5-Cl₂ 1.506C₆H₂-2,4,5-Cl₃ 1 2,6-Cl₂ 1.507 C₆H₂-2,4,5-Cl₃ 1 3,4-Cl₂ 1.508C₆H₂-2,4,5-Cl₃ 1 3,5-Cl₂ 1.509 C₆H₂-2,4,5-Cl₃ 1 3-CF₃ 1.510C₆H₂-2,4,5-Cl₃ 1 4-CF₃ 1.511 C₆H₃-2-OCH₃-5-Br 0 H 1.512 C₆H₃-2-OCH₃-5-Br0 2-F 1.513 C₆H₃-2-OCH₃-5-Br 0 3-F 1.514 C₆H₃-2-OCH₃-5-Br 0 4-F 1.515C₆H₃-2-OCH₃-5-Br 0 2-Cl 1.516 C₆H₃-2-OCH₃-5-Br 0 3-Cl 1.517C₆H₃-2-OCH₃-5-Br 0 4-Cl 1.518 C₆H₃-2-OCH₃-5-Br 0 2,3-Cl₂ 1.519C₆H₃-2-OCH₃-5-Br 0 2,4-Cl₂ 1.520 C₆H₃-2-OCH₃-5-Br 0 2,5-Cl₂ 1.521C₆H₃-2-OCH₃-5-Br 0 2,6-Cl₂ 1.522 C₆H₃-2-OCH₃-5-Br 0 3,4-Cl₂ 1.523C₆H₃-2-OCH₃-5-Br 0 3,5-Cl₂ 1.524 C₆H₃-2-OCH₃-5-Br 0 3-CF₃ 1.525C₆H₃-2-OCH₃-5-Br 0 4-CF₃ 1.526 C₆H₃-2-OCH₃-5-Br 1 H 1.527C₆H₃-2-OCH₃-5-Br 1 2-F 1.528 C₆H₃-2-OCH₃-5-Br 1 3-F 1.529C₆H₃-2-OCH₃-5-Br 1 4-F 1.530 C₆H₃-2-OCH₃-5-Br 1 2-Cl 1.531C₆H₃-2-OCH₃-5-Br 1 3-Cl 1.532 C₆H₃-2-OCH₃-5-Br 1 4-Cl 1.533C₆H₃-2-OCH₃-5-Br 1 2,3-Cl₂ 1.534 C₆H₃-2-OCH₃-5-Br 1 2,4-Cl₂ 1.535C₆H₃-2-OCH₃-5-Br 1 2,5-Cl₂ 1.536 C₆H₃-2-OCH₃-5-Br 1 2,6-Cl₂ 1.537C₆H₃-2-OCH₃-5-Br 1 3,4-Cl₂ 1.538 C₆H₃-2-OCH₃-5-Br 1 3,5-Cl₂ 1.539C₆H₃-2-OCH₃-5-Br 1 3-CF₃ 1.540 C₆H₃-2-OCH₃-5-Br 1 4-CF₃ 1.541 1-naphthyl0 H 1.542 1-naphthyl 0 2-F 1.543 1-naphthyl 0 3-F 1.544 1-naphthyl 0 4-F1.545 1-naphthyl 0 2-Cl 1.546 1-naphthyl 0 3-Cl 1.547 1-naphthyl 0 4-Cl1.548 1-naphthyl 0 2,3-Cl₂ 1.549 1-naphthyl 0 2,4-Cl₂ 1.550 1-naphthyl 02,5-Cl₂ 1.551 1-naphthyl 0 2,6-Cl₂ 1.552 1-naphthyl 0 3,4-Cl₂ 1.5531-naphthyl 0 3,5-Cl₂ 1.554 1-naphthyl 0 3-CF₃ 1.555 1-naphthyl 0 4-CF₃1.556 1-naphthyl 1 H 1.557 1-naphthyl 1 2-F 1.558 1-naphthyl 1 3-F 1.5591-naphthyl 1 4-F 1.560 1-naphthyl 1 2-Cl 1.561 1-naphthyl 1 3-Cl 1.5621-naphthyl 1 4-Cl 1.563 1-naphthyl 1 2,3-Cl₂ 1.564 1-naphthyl 1 2,4-Cl₂1.565 1-naphthyl 1 2,5-Cl₂ 1.566 1-naphthyl 1 2,6-Cl₂ 1.567 1-naphthyl 13,4-Cl₂ 1.568 1-naphthyl 1 3,5-Cl₂ 1.569 1-naphthyl 1 3-CF₃ 1.5701-naphthyl 1 4-CF₃

BIOLOGICAL EXAMPLES

A. Control of Animal Parasites

Example B.1 In-Vivo Test Against Trichostrongylus colubriformis andHaemonchus contortus in Mongolian Gerbils (Meriones unguiculatus) onPeroral Administration

Six to eight week-old Mongolian gerbils are infected by artificialfeeding with about 2000 larvae each of the 3rd stage of T. colubriformisand H. contortus. 6 days after infection, the gerbils are lightlyanaesthetized with N₂O and treated by peroral administration with thetest compounds, dissolved in a mixture of 2 parts of DMSO and 1 part ofpolyethylene glycol (PEG 300), using amounts of 100, 32 and 10-0.1mg/kg. On day 9 (3 days after treatment), when most of the H. contortuslarvae of the late 4th stage and most of the T. colubriformis areimmature adults, the gerbils are killed to count the worms. The efficacyis calculated in % reduction of the number of worms in each gerbil bycomparison with the geometric mean of the number of worms of 8 infectedand untreated gerbils.

A strong reduction of the nematode attack is achieved in this test withcompounds of the formula (I).

B. Control of Plant Pests

Example B.2 Action against Heliothis virescens Caterpillars

Young soybean plants are sprayed with an aqueous emulsion spray mixturecomprising 400 ppm of active ingredient and, after the spray-coating hasdried, are populated with 10 caterpillars of Heliothis virescens in thefirst stage and then placed in a plastics container.

Evaluation is carried out 6 days later. The percentage reduction inpopulation and in feeding damage (% activity) are determined bycomparing the number of dead caterpillars and the feeding damage on thetreated plants with that on untreated plants. The compounds of theTables exhibit good activity against Heliothis virescens in this test.

Example B.3 Action against Plutella xylostella Caterpillars

Young cabbage plants are sprayed with an aqueous emulsion spray mixturecomprising 400 ppm of active ingredient and, after the spray-coating hasdried, are populated with 10 caterpillars of Plutella xylostella in thethird stage and then placed in a plastics container. Evaluation iscarried out 3 days later. The percentage reduction In population and infeeding damage (% activity) are determined by comparing the number ofdead caterpillars and the feeding damage on the treated plants with thaton untreated plants.

The compounds of the Tables exhibit good activity against Plutellaxylostella.

Example B.4 Action Against Diabrotica balteata Larvae

Maize seedlings are sprayed with an aqueous emulsion spray mixturecomprising 400 ppm of active ingredient and, after the spray-coating hasdried, are populated with 10 larvae of Diabrotica balteata in the secondstage and then placed in a plastics container. Evaluation is carried out6 days later. The percentage reduction in population (% activity) isdetermined by comparing the number of dead larvae on the treated plantswith that on untreated plants. The compounds of the Tables exhibit goodactivity against Diabrotica balteata in this test.

1. Compound of the formula (I)

in which R₁ is aryl or heteroaryl, in each case unsubstituted or mono-or polysubstituted by R₇, where the substituents can in each case beidentical or different if their number is greater than 1; R₂ isC₁-C₆alkyl, halo-C₁-C₆alkyl, C₃-C₈cycloalkyl, halo-C₃-C₈cycloalkyl,NHR₈, aryl or heteroaryl, in each case unsubstituted or mono- orpolysubstituted by R₇, where the substituents can in each case beidentical or different if their number is greater than 1, orpyrrolidinyl, piperidinyl, imidazolidinyl, piperazinyl, pyrazolidinyl,morpholinyl, indolinyl or isoindolinyl, in each case bonded via N; R₃ ishydrogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkyl, benzyl,C₁-C₆alkylheteroaryl, C₁-C₆alkoxycarbonyl or C₁-C₆alkylcarbonyl; R₄, R₅and R₆ either independently of one another are hydrogen, halogen,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₂-C₆alkenyl, C₂-C₆alkynyl,unsubstituted or substituted C₃-C₈cycloalkyl, where the substituents areselected from the group consisting of halogen and C₁-C₆alkyl, orunsubstituted or substituted phenyl, where the substituents are selectedfrom the group consisting of halogen, C₁-C₆alkyl and phenyl; or R₄ andR₅, together with the carbon atoms to which they are bonded, are a five-to seven-membered, saturated or partially unsaturated heterocyclic ringhaving 1 to 2 heteroatoms from the group consisting of nitrogen, oxygenand sulphur; R₇ is halogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,halo-C₁-C₆alkoxy, C₁-C₆alkylthio, halo-C₁-C₆alkylthio, C₂-C₆alkenyl,C₂-C₆alkynyl; aryl, phenylacetylenyl or heteroaryl, in each caseunsubstituted or mono- or polysubstituted, where the substituents are ineach case selected from the group consisting of halogen, nitro, cyano,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy, and can ineach case be identical or different if their number is greater than 1;R₈ is aryl which is unsubstituted or mono- to pentasubstituted, wherethe substituents are selected from the group consisting of halogen,nitro, cyano, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy andhalo-C₁-C₆alkoxy, and can be identical or different if their number isgreater than 1; X is O, S, S(O) or S(O)₂; and n is 1; and, whereappropriate, E/Z isomers, mixtures of E/Z isomers and/or tautomersthereof, in each case in free form or in salt form.
 2. Compound of theformula (I) according to claim 1, wherein R₁ is aryl which isunsubstituted or mono- to penta-substituted by R₇, where thesubstitutents in each case can be identical or different if their numberis greater than
 1. 3. Compound of the formula (I) according to claim 1,wherein R₁ is aryl which is mono- to trisubstituted by R₇, where thesubstituents in each case can be identical or different if their numberis greater than
 1. 4. Compound of the formula (I) according to claim 1,wherein R₂ is C₁-C₆alkyl, halo-C₁-C₆alkyl, aryl or heteroaryl which isin each case unsubstituted or mono- to polysubstituted by R₇, where thesubstituents can in each case be identical or different if their numberis greater than
 1. 5. Compound of the formula (I) according to claim 1,wherein R₂ is C₁-C₆alkyl, halo-C₁-C₆alkyl or aryl which is unsubstitutedor mono- to pentasubstituted by R₇, where the substituents can beidentical or different if their number is greater than
 1. 6. Compound ofthe formula (I) according to claim 1, wherein R₂ is aryl which isunsubstituted or mono- to trisubstituted by R₇, where the substituentscan be identical or different if their number is greater than
 1. 7.Compound of the formula (I) according to claim 1, wherein R₃ is hydrogenor C₁-C₆alkyl.
 8. Compound of the formula (I) according to claim 1,wherein R₃ is hydrogen or C₁-C₄alkyl.
 9. Compound of the formula (I)according to claim 1, wherein R₃ is hydrogen.
 10. Compound of theformula (I) according to claim 1, wherein R₄, R₅ and R₆ independently ofone another are hydrogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,halo-C₁-C₆alkoxy, C₂-C₆alkenyl, C₂-C₆-alkynyl, C₃-C₆cycloalkyl. 11.Compound of the formula (I) according to claim 1, wherein R₄, R₅ and R₆independently of one another are hydrogen, C₁-C₄alkyl, halo-C₁-C₄alkylor C₃-C₆cycloalkyl.
 12. Compound of the formula (I) according to claim1, wherein R₄, R₅ and R₆ independently of one another are hydrogen orC₁-C₂alkyl.
 13. Compound of the formula (I) according to claim 1,wherein R₇ is halogen, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄-alkoxy,halo-C₁-C₄alkoxy; aryl or phenylacetylenyl, in each case unsubstitutedor mono- or polysubstituted, where the substituents are selected fromthe group consisting of halogen, C₁-C₆alkyl, halo-C₁-C₆alkyl,C₁-C₆alkoxy, halo-C₁-C₆alkoxy, and can in each case be identical ordifferent if their number is greater than
 1. 14. Compound of the formula(I) according to claim 1, wherein R₇ is halogen, C₁-C₂alkyl,halo-C₁-C₂alkyl, C₁-C₂alkoxy, halo-C₁-C₂alkoxy.
 15. Compound of theformula (I) according to claim 1, wherein R₇ is halogen orhalo-C₁-C₂alkyl.
 16. Compound of the formula (I) according to claim 1,wherein R₈ is unsubstituted or mono- to trisubstituted aryl, where thesubstituents are selected from the group consisting of halogen,C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy and halo-C₁-C₄alkoxy, and canbe identical or different if their number is greater than
 1. 17.Compound of the formula (I) according to claim 1, wherein R₈ is mono- totrisubstituted aryl, where the substituents are selected from the groupconsisting of halogen, C₁-C₂alkyl, halo-C₁-C₂alkyl, andhalo-C₁-C₂alkoxy, and can be identical or different if their number isgreater than
 1. 18. Compound of the formula (I) according to claim 1,wherein R₈ is mono- or disubstituted aryl, where the substituents areselected from the group consisting of halogen and halo-C₁-C₂alkyl, andcan be identical or different if their number is greater than
 1. 19.Compound of the formula (I) according to claim 1, wherein X is O or S.20. Compound of the formula (I) according to claim 1, wherein X is O.21. (canceled)
 22. Compound of the formula (I) according to claim 1,wherein R₁ is aryl which is unsubstituted or mono- or pentasubstitutedby R₇, where the substituents can in each case be identical or differentif their number is greater than 1; R₂ is C₁-C₆alkyl, halo-C₁-C₆alkyl,aryl or heteroaryl, in each case unsubstituted or mono- orpolysubstituted by R₇, where the substituents can in each case beidentical or different if their number is greater than 1; R₃ is hydrogenor C₁-C₆alkyl; R₄, R₅ and R₆ independently of one another are hydrogen,C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy, halo-C₁-C₆alkoxy,C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl; R₇ is halogen, C₁-C₄alkyl,halo-C₁-C₄alkyl, C₁-C₄alkoxy, halo-C₁-C₄alkoxy, aryl orphenylacetylenyl, in each case unsubstituted or mono- orpolysubstituted, where the substituents are selected from the groupconsisting of halogen, C₁-C₆alkyl, halo-C₁-C₆alkyl, C₁-C₆alkoxy,halo-C₁-C₆alkoxy, and in each case can be identical or different iftheir number is greater than 1; R₈ is unsubstituted or mono- totrisubstituted aryl, where the substituents are selected from the groupconsisting of halogen, C₁-C₄alkyl, halo-C₁-C₄alkyl, C₁-C₄alkoxy andhalo-C₁-C₄alkoxy, and can be identical or different if their number isgreater than 1; and X is O or S.
 23. Compound of the formula (I)according to claim 1, wherein R₁ is aryl which is mono- ortrisubstituted by R₇, where the substituents can in each case beidentical or different if their number is greater than 1; R₂ isC₁-C₆alkyl, halo-C₁-C₆alkyl or aryl which is unsubstituted or mono- topentasubstituted by R₇, where the substituents can be identical ordifferent if their number is greater than 1; R₃ is hydrogen orC₁-C₄alkyl; R₄, R₅ and R₆ independently of one another are hydrogen,C₁-C₄alkyl, halo-C₁-C₄alkyl or C₃-C₆cycloalkyl; R₇ is halogen,C₁-C₂alkyl, halo-C₁-C₂alkyl, C₁-C₂alkoxy or halo-C₁-C₂alkoxy; R₈ ismono- to trisubstituted aryl, where the substituents are selected fromthe group consisting of halogen, C₁-C₂alkyl, halo-C₁-C₂alkyl, andhalo-C₁-C₂alkoxy, and can be identical or different if their number isgreater than 1; and X is O.
 24. Compound of the formula (I) according toclaim 1, wherein R₁ is aryl which is mono- to trisubstituted by R₇,where the substituents can in each case be identical or different iftheir number is greater than 1; R₂ is aryl which is unsubstituted ormono- to trisubstituted by R₇, where the substituents can in each casebe identical or different if their number is greater than 1; R₃ ishydrogen; R₄, R₅ and R₆ independently of one another are hydrogen orC₁-C₂alkyl; R₇ is halogen or halo-C₁-C₂alkyl; R₈ is mono- ordisubstituted aryl, where the substituents are selected from the groupconsisting of halogen and halo-C₁-C₂alkyl, and can be identical ordifferent if their number is greater than 1; and X is O.
 25. Compound ofthe formula (I) according to claim 1, namedN-(1-cyano-1-[2,3-dichlorophenoxymethyl]ethyl)-C-phenylmethanesulphonamide.26. Process for the preparation of compounds of the formula (I), in eachcase in free form or in salt form, according to claim 1, characterizedin that a compound of the formula (II)

which is known or can be prepared in analogy to corresponding knowncompounds and in which R₁, R₃, R₄, R₅, R₆, X and n are as defined forthe formula (I), is reacted with a compound of the formula (III)

which is known or can be prepared in analogy to corresponding knowncompounds and in which R₂ are as defined for the formula (I) and Q is aleaving group, if appropriate in the presence of a basic catalyst, andin each case, if desired, a compound of the formula (I), in each case infree form or in salt form, obtainable according to the process or inanother manner, is converted into another compound of the formula (I), amixture of isomers obtainable according to the process is separated andthe desired isomer is isolated and/or a free compound of the formula (I)obtainable according to the process is converted into a salt or a saltof a compound of the formula (I) obtainable according to the process isconverted into the free compound of the formula (I) or into anothersalt.
 27. Composition for the control of parasites, which, in additionto carriers and/or dispersants, contains as active compound at least onecompound of the formula (I) according to claim
 1. 28-31. (canceled) 32.A method for controlling parasites comprising applying to said parasitesor its habitat a parasiticidal effective amount of at least one compoundof formula I of claim
 1. 33. The method of claim 33 wherein saidparasiticidal effective amount of said at least one compound of formulaI of claim 1 is administered to an animal host of said parasite.
 34. Themethod of claim 33 whereby said at least one compound of formula I ofclaim 1 is administered to said animal host topically, perorally,parenterally, or subcutaneously.
 35. The method of claim 32 whereby saidcompound is in a formulation consisting of the group of pour-on,spot-on, tablet, chewie, powder, boli, capsules, suspension, emulsion,solution, injectable, water-additive, and food-additive.
 36. The methodof claim 32 wherein said parasites are endo-parasites.
 37. The method ofclaim 36 wherein said endo-parasites are helminthes.
 38. A method oftreating an animal for parasites comprising administering to said animalin need of treatment thereof a parasiticidal effective amount of thecomposition of claim
 27. 39. The method of claim 38 wherein saidadministration to said animal is topically, perorally, parenterally, orsubcutaneously.
 40. The method of claim 38 wherein said composition ofclaim 27 is in a formulation consisting of the group of pour-on,spot-on, tablet, chewie, powder, boli, capsules, suspension, emulsion,solution, injectable, water-additive, and food-additive.
 41. The methodof claim 38 wherein said parasites are endo-parasites.
 42. The method ofclaim 41 wherein said endo-parasites are helminthes.